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Synthesis of glycolipids

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Carbohydrate Chemistry

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 154))

Abstract

The chemical syntheses of the carbohydrate portions of the naturally occurring glycolipids derived from the sphingosine bases (as well as the syntheses of the complete glycosphingolipids) and of myoinositol-containing lipids derived from esters of glycerol, which were reported between 1977 and 1987, are reviewed. This article therefore brings up to date a previous review published in Chemistry and Physics of Lipids (1980) 26: 287. Since this is a very active field of research, most of the new synthetic techniques introduced into carbohydrate chemistry in the last decade are discussed. The syntheses of sphingosine bases and glycerol derivatives from carbohydrate precursors acting as ‘chiral templates’ are also reviewed with a more historical perspective.

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9 References

  1. Gigg R (1980) Chem Phys Lipids 26: 287

    CAS  Google Scholar 

  2. Ishizuka I, Yamakawa T (1985) Glycoglycerolipids, in: Wiegandt H (ed) Glycolipids Elsevier, Amsterdam, p 101

    Google Scholar 

  3. Gigg J, Gigg R (in press) Synthesis of glycoglycerolipids, in: Handbook of lipid research, Glycoglycerolipids (ed) Kates M, Plenum, New York

    Google Scholar 

  4. Gigg J, Gigg R, Payne S, Conant R (1986) Synthetic studies on the major serologically active glycolipid from Mycobacterium leprae, in: Klein RA, Schmitz B (eds) Topics in lipid research — from structural elucidation to biological function, Royal Society of Chemistry p. 119

    Google Scholar 

  5. Anderson L, Unger FM (1983) Bacterial lipopolysaccharides, ACS Symp Ser 231

    Google Scholar 

  6. Morrison DC, Alving CR (1984) Molecular concepts of lipid A, Rev Infect Diseases 6: 427

    Google Scholar 

  7. Imoto M, Kusumoto S, Shiba T, Rietschel ET, Galanos C, Lüderitz O (1985) Tetrahedron Lett 26: 907

    CAS  Google Scholar 

  8. Imoto M, Yoshimura H, Sakaguchi N, Kusumoto S, Shiba T (1985) Tetrahedron Lett 26: 1545

    CAS  Google Scholar 

  9. Takahashi T, Nakamoto S, Ikeda K, Achiwa K (1986) Tetrahedron Lett 27: 1819

    CAS  Google Scholar 

  10. Kiso M, Tanaka S, Tanahashi M, Fujishima Y, Ogawa Y, Hasegawa A (1986) Carbohydr Res 148: 221

    CAS  Google Scholar 

  11. Paulsen H, Stiem M, Unger FM (1986) Tetrahedron Lett 27: 1135

    CAS  Google Scholar 

  12. Weigandt H (1985) Glycolipids Elsevier Amsterdam

    Google Scholar 

  13. Kanfer JN, Hakomori S (eds) (1983) Handbook of lipid research, vol. 3, Sphingolipid biochemistry, Plenum, New York

    Google Scholar 

  14. Gigg R (1983) Phospholipids and Glycolipids, in: Ansell MF (ed) Supplement to 2nd ed of Rodd’s Chemistry of Carbon Compounds vol 1E, Elsevier, Amsterdam, p 425

    Google Scholar 

  15. Hakomori S (1984) Ann Rev Immunol 2: 103

    CAS  Google Scholar 

  16. Hakomori S (1986) Chem Phys Lipids 42: 209

    CAS  Google Scholar 

  17. Makita A, Handa S, Taketomi T, Nagai Y (eds) (1982) New vistas in glycolipid research, Plenum, New York.

    Google Scholar 

  18. Hakomori S (1981) Ann Rev Biochem 50: 733

    CAS  Google Scholar 

  19. Hakomori S, Kannagi R (1986) Carbohydrate antigens in higher animals, in: Weir, DM (ed) Handbook of experimental immunology vol 1, Chap 9, Blackwell, Oxford

    Google Scholar 

  20. Weigandt H (1982) Adv Neurochem 4: 149

    Google Scholar 

  21. Walborg EF (ed) Glycoproteins and glycolipids in disease processes, ACS Symp Ser 80 1979

    Google Scholar 

  22. Paulsen H (1977) Pure and Appl Chem 49: 1169

    CAS  Google Scholar 

  23. Paulsen H (1982) Angew Chem, Int Ed Engl 21: 155

    Google Scholar 

  24. Paulsen H (1984) Chem Soc Rev 13: 15

    CAS  Google Scholar 

  25. Lemieux RU (1978) Chem Soc Rev 7: 423

    CAS  Google Scholar 

  26. Sinaÿ PA (1978) Pure and Appl Chem 50: 1437

    Google Scholar 

  27. Ogawa T, Yamamoto H, Nukada T, Kitajima T, Sugimoto M, (1984) Pure and Appl Chem 56: 779

    CAS  Google Scholar 

  28. Schmidt RR (1986) Angew Chem, Int Ed Engl 25: 212

    Google Scholar 

  29. van Boeckel CAA, Beetz T (1985) Recl Trav Chim Pays-Bas 104: 171, 174

    Google Scholar 

  30. van Boeckel CAA, Beetz T, van Aelst SF (1984) Tetrahedron 40: 4097

    Google Scholar 

  31. Garegg PJ (1984) Pure and Appl Chem 56: 845

    CAS  Google Scholar 

  32. van Boeckel CAA (1986) Recl Trav Chim 105: 35

    Google Scholar 

  33. Baer E, Fischer HOL (1939) J Biol Chem 128: 463

    CAS  Google Scholar 

  34. Gigg R, Warren CD, Cunningham J (1965) Tetrahedron Lett 1303

    Google Scholar 

  35. Gigg J, Gigg R, Warren CD (1966) J Chem Soc C 1872

    Google Scholar 

  36. Konstas S, Photaki I, Zervas L (1959) Chem Ber 92: 1288

    CAS  Google Scholar 

  37. Gigg J, Gigg R (1966) J Chem Soc C 1876

    Google Scholar 

  38. Mulzer J, Brand C (1986) Tetrahedron 42: 5961

    CAS  Google Scholar 

  39. Reist EJ, Christie PH (1970) J Org Chem 35: 3521

    CAS  Google Scholar 

  40. Reist EJ, Christie PH (1970) ibid 35 4127

    CAS  Google Scholar 

  41. Koike K, Nakahara Y, Ogawa T (1984) Glycoconjugate J 1: 107

    CAS  Google Scholar 

  42. Koike K, Numata M, Nakahara Y, Ogawa T (1986) Carbohydr Res 158: 113

    CAS  Google Scholar 

  43. Obayashi M, Schlosser M (1985) Chem Lett 1715

    Google Scholar 

  44. Schmidt RR, Zimmermann P (1986) Tetrahedron Lett 27: 481

    CAS  Google Scholar 

  45. Kiso M, Nakamura A, Nakamura J, Tomita Y, Hasegawa A (1986) J Carbohydr Chem 5: 335

    CAS  Google Scholar 

  46. Kiso M, Nakamura A, Tomita Y, Hasegawa A (1986) Carbohydr Res 158: 101

    CAS  Google Scholar 

  47. Gigg R, Conant R (1977) J Chem Soc, Perkin 1: 2006

    Google Scholar 

  48. Corey EJ, Winter RAE (1963) J Am Chem Soc 85: 2677

    CAS  Google Scholar 

  49. Corey EJ, Hopkins PB (1982) Tetrahedron Lett 23, 1979

    CAS  Google Scholar 

  50. Shapiro D, Flowers HM, Spector-Shefer S (1959) J Am Chem Soc 81: 4360

    CAS  Google Scholar 

  51. Shapiro D, Flowers HM (1962) ibid 84: 1047

    CAS  Google Scholar 

  52. Funaki Y, Kawai G, Mori K (1986) Agric Biol Chem 50: 615

    CAS  Google Scholar 

  53. Mori K, Funaki Y (1985) Tetrahedron 41: 2369

    CAS  Google Scholar 

  54. Garigipati RS, Weinreb SM (1983) J Am Chem Soc 105: 4499

    CAS  Google Scholar 

  55. Tkaczuk P, Thornton ER (1981) J Org Chem 46: 4393

    CAS  Google Scholar 

  56. Mori K, Umemura T (1982) Tetrahedron Lett 23: 3391

    CAS  Google Scholar 

  57. Roush WR, Adam MA (1985) J Org Chem 50: 3752

    CAS  Google Scholar 

  58. Julina R, Herzig T, Bernet B, Vasella A (1986) Helv Chim Acta 69: 368

    CAS  Google Scholar 

  59. Cardillo G, Orena M, Sandri S, Tomasini C (1986) Tetrahedron 42: 917

    CAS  Google Scholar 

  60. Hino T, Nakayama K, Taniguchi M, Nakagawa M (1986) J Chem Soc, Perkin Trans 1: 1687

    Google Scholar 

  61. Kulmacz RJ, Kisic A, Schroepfer GJ (1979) Chem Phys Lipids 23: 291

    CAS  Google Scholar 

  62. Shoyama Y, Okabe H, Kishimoto Y, Costello C (1978) J Lipid Res 19: 250

    CAS  Google Scholar 

  63. Hirth G, Walter W (1985) Helv Chim Acta 68: 1863

    CAS  Google Scholar 

  64. Jurczak J, Pikul S, Baner T (1986) Tetrahedron 42: 447

    CAS  Google Scholar 

  65. Takano S, Kurotaki A, Takahashi M, Ogasawara K (1986) Synthesis 403

    Google Scholar 

  66. Jung ME, Shaw TJ (1980) J Am Chem Soc 102: 6304

    CAS  Google Scholar 

  67. Takano S, Numata H, Ogasawara K (1982) Heterocycles 19: 327

    CAS  Google Scholar 

  68. Hubschwerlen C (1986) Synthesis 962

    Google Scholar 

  69. Kanda P, Wells MA (1980) J Lipid Res 21: 257

    CAS  Google Scholar 

  70. Gigg R (1979) J Chem Soc, Perkin Trans 1: 712

    Google Scholar 

  71. Eibl H, Woolley P (1986) Chem Phys Lipids 41: 53

    CAS  Google Scholar 

  72. Wiggins LF (1946) J Chem Soc 13

    Google Scholar 

  73. Bering HFG, Boren HB, Garegg PJ (1967) Acta Chem Scand 21: 2083

    Google Scholar 

  74. van Boeckel CAA, Visser GM, van Boom JH (1985) Tetrahedron 41: 4557

    Google Scholar 

  75. Gent PA, Gigg R (1976) Chem Phys Lipids 17: 111

    CAS  Google Scholar 

  76. van Boeckel CAA, van Boom JH (1985) Tetrahedron 41: 4545

    Google Scholar 

  77. Ness AT, Hann RM, Hudson CS (1943) J Am Chem Soc 65: 2215

    CAS  Google Scholar 

  78. Wickberg B (1958) Acta Chem Scand 12: 1187

    CAS  Google Scholar 

  79. Gigg J, Gigg R (1967) J Chem Soc C: 1865

    Google Scholar 

  80. Wehrli HP, Pomeranz Y (1969) Chem Phys Lipids 3: 357

    CAS  Google Scholar 

  81. Schmidt RR, Kläger R (1985) Angew Chem, Int Ed Engl 24: 65

    Google Scholar 

  82. Schmidt RR, Zimmerman P (1986) ibid 25: 725

    Google Scholar 

  83. Koike K, Sugimoto M, Nakahara Y, Ogawa T (1985) Glycoconjugate J 2: 105

    Google Scholar 

  84. Mori K, Funaki Y (1985) Tetrahedron 41: 2379

    CAS  Google Scholar 

  85. Kawai G, Ikeda Y (1985) J Lipid Res 26: 338

    CAS  Google Scholar 

  86. Gal AE, Pentchev PG, Massey JM, Brady RO (1979) Proc Nat Acad Sci 76: 3083

    CAS  Google Scholar 

  87. Carter HE, Rothfus JA, Gigg R (1961) J Lipid Res 2: 228

    Google Scholar 

  88. Yoshino T, Watanabe K, Hakomori S (1982) Biochemistry 21: 928

    CAS  Google Scholar 

  89. Weis AL, Brady RO, Shapiro D (1985) Chem Phys Lipids 38: 391

    CAS  Google Scholar 

  90. Koshy KM, Boggs JM (1983) ibid 34: 41

    CAS  Google Scholar 

  91. Ariga T, Murata T, Oshima M, Maezawa M, Miyatake T (1980) J Lipid Res 21: 879

    CAS  Google Scholar 

  92. Cioffi EA, Prestegard JH (1986) Tetrahedron Lett 27: 415

    CAS  Google Scholar 

  93. Usuki S, Nagai Y (1986) Analytical Biochem 152: 172

    CAS  Google Scholar 

  94. Ogura H, Furuhata K, Itoh M, Shitori Y (1986) Carbohydr Res 158: 37

    CAS  Google Scholar 

  95. Ito Y, Sugimoto M, Sato S, Ogawa T (1986) Tetrahedron Lett 27: 4753

    CAS  Google Scholar 

  96. Kanemitsu K, Sweeley CC (1986) Glycoconjugate J 3: 143

    CAS  Google Scholar 

  97. Sato S, Ito Y, Ogawa T (1986) Carbohydr Res 155: C1

    Google Scholar 

  98. Sato S, Mori M, Ito Y, Ogawa T (1986) ibid 155: C6

    Google Scholar 

  99. Ek M, Garegg PJ, Oscarson S (1983) J Carbohydr Chem 2: 305

    CAS  Google Scholar 

  100. Paulsen H, Hadamczyk D, Kutschker W, Bünsch A (1985) Annalen 129

    Google Scholar 

  101. Paulsen H, Paal M (1985) Carbohydr Res 137: 39

    CAS  Google Scholar 

  102. Alais J, Maranduba A, Veyrières A (1983) Tetrahedron Lett 24: 2383

    CAS  Google Scholar 

  103. David S, Thieffry A, Veyrières A (1981) J Chem Soc, Perkin Trans 1: 1796

    Google Scholar 

  104. David S, Hanessian S (1985) Tetrahedron 41: 643

    CAS  Google Scholar 

  105. Maranduba A, Veyrières A (1986) Carbohydr Res 151: 105

    CAS  Google Scholar 

  106. Maranduba A, Veyrières A (1985) ibid: 135: 330

    CAS  Google Scholar 

  107. Sugimoto M, Horisaki T, Ogawa T (1985) Glycoconjugate J 2: 11

    CAS  Google Scholar 

  108. Ogawa T, Matsui M (1978) Carbohydr Res 62: C1

    Google Scholar 

  109. Ogawa T, Matsui M (1981) Tetrahedron 37: 2363

    CAS  Google Scholar 

  110. Veyrières A (1981) J Chem Soc, Perkin Trans 1: 1626

    Google Scholar 

  111. Paulsen H, Bünsch A (1982) Carbohydr Res 101: 21

    CAS  Google Scholar 

  112. Zurabyan SE, Markin VA, Pimenova VV, Rozynov BV, Sadovskaya VL, Khorlin AY (1978) Bioorg Khim 4: 928 (679)

    CAS  Google Scholar 

  113. Ponpipom MM, Bugianesi RL, Shen TY (1978) Tetrahedron Lett 1717

    Google Scholar 

  114. Garegg PJ, Hultberg H (1982) Carbohydr Res 110: 261

    CAS  Google Scholar 

  115. Jacquinet JC, Sinaÿ P (1985) ibid 143: 143

    CAS  Google Scholar 

  116. Cox DD, Metzner EK, Reist EJ (1978) ibid 63: 139

    CAS  Google Scholar 

  117. Martin-Lomas M, Bernabe M, Garcia-Montes P (1981) An Quim Ser C, 77: 230

    CAS  Google Scholar 

  118. Fernandez-Mayoralas A, Martin-Lomas M, Villanueva D (1985) Carbohydr Res 140: 81

    CAS  Google Scholar 

  119. Leontein K, Nilsson M, Norberg T (1985) ibid 144: 231

    CAS  Google Scholar 

  120. Garegg PJ, Hultberg H (1981) ibid 93: C10

    Google Scholar 

  121. Garegg PJ, Hultberg H, Wallin S (1982) ibid 108: 97

    CAS  Google Scholar 

  122. Wessel HP, Iversen T, Bundle DR (1984) ibid 130: 5

    CAS  Google Scholar 

  123. Banoub J, Bundle DR (1979) Can J Chem 57: 2085

    CAS  Google Scholar 

  124. Banoub J, Bundle DR (1979) ibid 57: 2091

    CAS  Google Scholar 

  125. Sabesan S, Lemieux RU (1984) ibid 62: 644

    CAS  Google Scholar 

  126. Takeo K, Tei S (1985) Carbohydr Res 141: 159

    CAS  Google Scholar 

  127. Takamura T, Chiba T, Ishihara H, Tejima S (1979) Chem Pharm Bull 27: 1497

    CAS  Google Scholar 

  128. Baer HH, Abbas SA (1979) Carbohydr Res 77: 117

    CAS  Google Scholar 

  129. Baer HH, Abbas SA (1980) ibid 84: 53

    CAS  Google Scholar 

  130. Hough L, Richardson AC, Thelwall LAW (1979) ibid 75: C11

    Google Scholar 

  131. Abbas SA, Barlow JJ, Matta KL (1981) ibid 88: 51

    CAS  Google Scholar 

  132. Karlsson KA (1986) Chem Phys Lipids 42: 153

    CAS  Google Scholar 

  133. de Graaf FK, Mooi FR (1986) Adv Microbial Physiol 26: 65

    Google Scholar 

  134. Cox DD, Metzner EK, Reist EJ (1978) Carbohydr Res 62: 245

    CAS  Google Scholar 

  135. Cox DD, Metzner EK, Cary LW, Reist EJ (1978) ibid 67: 23

    CAS  Google Scholar 

  136. Shapiro D, Acher AJ (1978) Chem Phys Lipids 22: 197

    CAS  Google Scholar 

  137. Chacon-Fuertes ME, Martin-Lomas M (1975) Carbohydr Res 43: 51

    CAS  Google Scholar 

  138. Milat ML, Zollo PA, Sinaÿ P (1982) ibid 100: 263

    CAS  Google Scholar 

  139. Dahmén J, Frejd T, Lave T, Lindh F, Magnusson G, Noori G, Pålsson K (1983) ibid 113: 219

    Google Scholar 

  140. Dahmén J, Frejd T, Grönberg G, Lave T, Magnusson G, Noori G (1983) ibid 116: 303

    Google Scholar 

  141. Dahmén J, Frejd T, Magnusson G, Noori G, (1982) ibid 111: C1

    Google Scholar 

  142. Dahmén J, Frejd T, Grönberg G, Lave T, Magnusson G, Noori G (1983) ibid 118: 292

    Google Scholar 

  143. Dahmén J, Frejd T, Magnusson G, Noori G, Carlström AS (1984) ibid 127: 15

    Google Scholar 

  144. Garegg PJ, Oscarson S (1985) ibid 137: 270

    CAS  Google Scholar 

  145. Garegg PJ, Samuelsson B (1979) J Chem Soc, Chem Commun 978

    Google Scholar 

  146. Kihlberg J, Frejd T, Jansson K, Magnusson G (1986) Carbohydr Res 152: 113

    CAS  Google Scholar 

  147. Wessel HP, Iversen T, Bundle DR (1985) J Chem Soc, Perkin Trans 1: 2247

    Google Scholar 

  148. Barton DHR, McCombie SW (1975) ibid 1574

    Google Scholar 

  149. Norberg T, Oscarson S, Szönyi M (1986) Carbohydr Res 152: 301

    CAS  Google Scholar 

  150. Jacquinet JC, Duchet D, Milat ML, Sinaÿ P (1981) J Chem Soc, Perkin Trans 1: 326

    Google Scholar 

  151. Petit JM, Jacquinet JC, Sinaÿ P (1980) Carbohydr Res 82: 130

    CAS  Google Scholar 

  152. Zollo PHA, Jacquinet JC, Sinaÿ (1983) ibid 122: 201

    CAS  Google Scholar 

  153. Dahmén J, Frejd T, Magnusson G, Noori G, Carlström AS (1984) ibid 129: 63

    Google Scholar 

  154. Dahmén J, Frejd T, Magnusson G, Noori G, Carlström AS (1984) ibid 125: 237

    Google Scholar 

  155. Nashed MA, Anderson L (1983) ibid 114: 43

    CAS  Google Scholar 

  156. Paulsen H, Kolář C (1981) Chem Ber 114: 306

    CAS  Google Scholar 

  157. Paulsen H, Bünsch H (1981) ibid 114: 3126

    CAS  Google Scholar 

  158. Lönn H (1985) Carbohydr Res 139: 105

    Google Scholar 

  159. Lemieux RU, Takeda T, Chung BY (1976) ACS Symp Ser 39: 90

    CAS  Google Scholar 

  160. Nashed MA (1979) Carbohydr Res 71: 299

    CAS  Google Scholar 

  161. Nashed MA, Slife CW, Kiso M, Anderson L (1980) ibid 82: 237

    CAS  Google Scholar 

  162. Nashed MA, El-Sokkary RI, Rateb L (1984) ibid 131: 47

    CAS  Google Scholar 

  163. Nashed MA, Anderson L (1983) ibid 114: 53

    CAS  Google Scholar 

  164. Paulsen H, Richter A, Sinnwell V, Stenzel W (1978) ibid 64: 339

    CAS  Google Scholar 

  165. Paulsen H, Kolář C, Stenzel W (1978) Chem Ber 111: 2358

    CAS  Google Scholar 

  166. Lemieux RU, Ratcliffe RM (1979) Can J Chem 57: 1244

    CAS  Google Scholar 

  167. Lemieux RU, Ratcliffe RM (1978) Ger Offen 2, 816, 340/1978; (1979) Chem Abs 90: 87846k

    Google Scholar 

  168. Lemieux RU, Stick RV (1978) Austral J Chem 31: 901

    CAS  Google Scholar 

  169. Bovin NV, Zurabyan SE, Khorlin AY (1979) Bioorg Khim 5: 1257 (945)

    CAS  Google Scholar 

  170. Bovin NV, Zurabyan SE, Khorlin AY (1981) Carbohydr Res 98: 25

    CAS  Google Scholar 

  171. Bovin NV, Zurabyan SE, Khorlin AY (1983) J Carbohydr Chem 2: 249

    CAS  Google Scholar 

  172. Lemieux RU, Abbas SZ, Burzynska MH, Ratcliffe RM (1982) Can J Chem 60: 63

    CAS  Google Scholar 

  173. Corey EJ, Suggs JW (1973) J Org Chem 38: 3224

    CAS  Google Scholar 

  174. Bundle DR, Josephson S (1979) Can J Chem 57: 662

    CAS  Google Scholar 

  175. Paulsen H, Paal M, Hadamczyk D, Steiger KM (1984) Carbohydr Res 131: C1

    Google Scholar 

  176. Excoffier G, Gagnaire D, Utille JP (1975) ibid 39: 368

    CAS  Google Scholar 

  177. Schmidt RR, Michel J (1980) Angew Chem, Int Ed Engl 19: 731

    Google Scholar 

  178. Osby JO, Martin MG, Ganen B (1984) Tetrahedron Lett 25: 2093

    CAS  Google Scholar 

  179. Rosenbrook W, Riley DA, Lartey PA (1985) ibid 26: 3

    CAS  Google Scholar 

  180. Posner GH, Haines SR (1985) ibid 26: 5

    CAS  Google Scholar 

  181. Paulsen H, Paal M (1984) Carbohydr Res 135: 53

    CAS  Google Scholar 

  182. Paulsen H, Bünsch A (1980) Angew Chem, Int Ed Engl 19: 902

    CAS  Google Scholar 

  183. Paulsen H, Lockhoff O (1981) Chem Ber 114: 3079

    CAS  Google Scholar 

  184. Paulsen H, Bünsch A (1981) Annalen 2204

    Google Scholar 

  185. Paulsen H, Röben W, Heiker FR (1980) Tetrahedron Lett 21: 3679

    CAS  Google Scholar 

  186. Paulsen H, Bünsch A (1982) Carbohydr Res 100: 143

    CAS  Google Scholar 

  187. Kijimoto-Ochiai S, Makita A, Bünsch A, Paulsen H (1983) Biochim Biophys Acta 756: 247

    CAS  Google Scholar 

  188. Luger P, Vangehr K, Bock K, Paulsen H (1983) Carbohydr Res 117: 23

    CAS  Google Scholar 

  189. David S, Lubineau A, Vatèle JM (1978) J Chem Soc Chem Commun 535

    Google Scholar 

  190. David S, Lubineau A, Vatèle JM (1980) Nouveau J Chim 4: 547

    CAS  Google Scholar 

  191. Paulsen H, Kolář C, Stenzel W (1978) Chem Ber 111: 2370

    CAS  Google Scholar 

  192. Paulsen H, Kolář C (1978) Angew. Chem, Int Ed Engl 17: 771

    Google Scholar 

  193. Paulsen H, Kolář C (1979) Chem Ber 112: 3190

    CAS  Google Scholar 

  194. Bovin NV, Zurabyan SE, Khorlin AY (1983) Carbohydr Res 112: 23

    CAS  Google Scholar 

  195. Bovin NV, Zurabyan SE, Khorlin AY (1982) Izvest Akad Nauk SSSR, Ser Khim 1148 (31D, 1023)

    Google Scholar 

  196. Lemieux RU, Abbas SZ, Chung BY (1982) Can J Chem 60: 68

    CAS  Google Scholar 

  197. Arnarp J, Lönngren J (1981) J Chem Soc, Perkin Trans 1: 2070

    Google Scholar 

  198. Ogawa T, Nakabayashi S (1981) Carbohydr Res 97: 81

    CAS  Google Scholar 

  199. Ogawa T, Nukada T, Matsui M (1982) ibid 101: 263

    CAS  Google Scholar 

  200. Ogawa T, Nakabayashi S, Sasajima K (1981) ibid 96: 29

    CAS  Google Scholar 

  201. Ogawa T, Nakabayashi S, Sasajima K (1981) ibid 95: 308

    CAS  Google Scholar 

  202. Augé C, David S, Veyrières A (1979) Nouveau J Chim 3: 491

    Google Scholar 

  203. Takamura T, Chiba T, Tejima S (1981) Chem Pharm Bull 29: 2270

    CAS  Google Scholar 

  204. Wood E, Feizi T (1979) FEBS Lett 104: 135

    CAS  Google Scholar 

  205. Alais J, Veyrières A (1981) Carbohydr Res 92: 310

    CAS  Google Scholar 

  206. Alais J, Veyrières A (1981) J Chem Soc, Perkin Trans 1: 377

    Google Scholar 

  207. Arnarp J, Lönngren J, Ottosson H (1981) Carbohydr Res 98: 154

    CAS  Google Scholar 

  208. Arnarp J, Haraldsson M, Lönngren J (1981) ibid 97: 307

    CAS  Google Scholar 

  209. Arnarp J, Lönngren J (1980) J Chem Soc, Chem Commun 1000

    Google Scholar 

  210. Alais J, Veyrières A (1981) Carbohydr Res 93: 164

    CAS  Google Scholar 

  211. Lee RT, Lee YC (1979) ibid 77: 270

    CAS  Google Scholar 

  212. Alais J, Veyrières A (1983) Tetrahedron Lett 24: 5223

    CAS  Google Scholar 

  213. Grundler G, Schmidt RR (1985) Carbohydr Res 135: 203

    CAS  Google Scholar 

  214. Augé C, Mathieu C, Mérienne C (1986) ibid 151: 147

    Google Scholar 

  215. Wong CH, Haynie SL, Whitesides GM (1982) J Org Chem 47: 5416

    CAS  Google Scholar 

  216. Whitesides GM, Wong CH (1985) Angew Chem, Int Ed Engl 24: 617

    Google Scholar 

  217. Augé C, David S, Mathieu C, Gautheron C (1984) Tetrahedron Lett 25: 1467

    Google Scholar 

  218. Takamura T, Chiba T, Tejima S (1979) Chem Pharm Bull 27: 721

    CAS  Google Scholar 

  219. Itoh Y, Tejima S (1983) ibid 31: 727

    CAS  Google Scholar 

  220. Jacquinet JC, Sinaÿ P (1979) Tetrahedron 35: 365

    CAS  Google Scholar 

  221. Milat ML, Sinaÿ P (1981) Carbohydr Res 92: 183

    CAS  Google Scholar 

  222. Jacquinet JC, Sinaÿ P (1979) J Chem Soc, Perkin Trans 1: 319

    Google Scholar 

  223. Augé C, Veyrières A (1979) ibid 1825

    Google Scholar 

  224. Subero C, Jimeno ML, Alemany A, Martin-Lomas M (1984) Carbohydr Res 126: 326

    CAS  Google Scholar 

  225. Paulsen H, Schnell D (1981) Chem Ber 114: 333

    CAS  Google Scholar 

  226. Hindsgaul O, Norberg T, Le Pendu J, Lemieux RU (1982) Carbohydr Res 109: 109

    CAS  Google Scholar 

  227. Lemieux RU, Wong TC, Thørgersen H (1982) Can J Chem 60: 81

    CAS  Google Scholar 

  228. Lemieux RU, Wong TC, Liao J, Kabat EA (1984) Molecular Immunol 21: 751

    CAS  Google Scholar 

  229. Khare DP, Hindsgaul O, Lemieux RU (1985) Carbohydr Res 136: 285

    CAS  Google Scholar 

  230. Rana SS, Vig R, Matta KL (1982) J Carbohydr Chem 1: 261

    Google Scholar 

  231. Jacquinet JC, Sinaÿ P (1979) J Chem Soc, Perkin Trans 1: 314

    Google Scholar 

  232. Pougny JR, Nassr MAM, Naulet N, Sinaÿ P (1978) Nouveau J Chim 2: 389

    CAS  Google Scholar 

  233. Bovin NV, Zurabayan SE, Khorlin AY (1980) Bioorg Khim 6: 242 (121)

    CAS  Google Scholar 

  234. Rana SS, Matta KL (1983) Carbohydr Res 117: 101

    CAS  Google Scholar 

  235. Rana SS, Barlow JJ, Matta KL (1981) ibid 96: 231

    CAS  Google Scholar 

  236. Horton D, Lehmann J (1978) ibid 61: 553

    CAS  Google Scholar 

  237. Benzing-Nguyen L, Perry MB (1978) J Org Chem 43: 551

    CAS  Google Scholar 

  238. Beau JM, Sinaÿ P (1978) Carbohydr Res 65: 1

    CAS  Google Scholar 

  239. Beau JM, Sinaÿ P, Kamerling JP, Vliegenthart FG (1978) ibid 67: 65

    CAS  Google Scholar 

  240. Augé C, David S, Gautheron C (1984) Tetrahedron Lett 25: 4663

    Google Scholar 

  241. Augé C, David S, Gautheron C, Veyrières A (1985) ibid 26: 2439

    Google Scholar 

  242. Danishefsky SJ, DeNinno MP (1986) J Org Chem 51: 2615

    CAS  Google Scholar 

  243. Baumberger F, Vasella A (1986) Helv Chim Acta 69: 1205

    CAS  Google Scholar 

  244. Baumberger F, Vasella A (1986) ibid 69: 1205

    CAS  Google Scholar 

  245. Hagedorn HW, Brossmer R (1986) ibid 69: 2127

    CAS  Google Scholar 

  246. Mack H, Brossmer R (1987) Tetrahedron Lett 28: 191

    CAS  Google Scholar 

  247. Vliegenthart JFG, Kamerling JP (1982) Synthesis of sialic acids and sialic acid derivatives, in: Schauer R (ed) Sialic acids, chemistry, metabolism and function Springer-Verlag, New York, p 59

    Google Scholar 

  248. Martin JE, Tanenbaum SW, Flashner M (1977) Carbohydr Res 56: 423

    CAS  Google Scholar 

  249. Czarniecki MF, Thornton ER (1977) J Am Chem Soc 99: 8273

    CAS  Google Scholar 

  250. Sharma MN, Eby R (1984) Carbohydr Res 127: 201

    CAS  Google Scholar 

  251. Eschenfelder V, Brossmer R (1979) Z physiol Chem 360: 1253

    CAS  Google Scholar 

  252. Eschenfelder V, Brossmer R (1980) Carbohydr Res 78: 190

    CAS  Google Scholar 

  253. Beau JM, Schauer R, Haverkamp J, Dorland L, Vliegenthart JFG, Sinaÿ P (1980) ibid 82: 125

    CAS  Google Scholar 

  254. van der Vleugel DJM, van Heeswijk WAR, Vliegenthart JFG (1982) ibid 102: 121

    Google Scholar 

  255. Hasegawa A, Nakamura J, Kiso M (1986) J Carbohydr Chem 5: 11

    CAS  Google Scholar 

  256. van der Vleugel DJM, Wassenburg FR, Zwikker JW, Vliegenthart JFG (1982) Carbohydr Res 104: 221

    Google Scholar 

  257. van der Vleugel DJM, Zwikker JW, Vilegenthart JFG, van Boeckel CAA, van Boom JH (1982) ibid 105: 19

    Google Scholar 

  258. Brandstetter HH, Zbiral E (1983) Monatshefte 114: 1247

    CAS  Google Scholar 

  259. Paulsen H, Tietz H (1982) Angew Chem, Int Ed Engl 21: 927

    Google Scholar 

  260. Paulsen H, Tietz H (1984) Carbohydr Res 125: 47

    CAS  Google Scholar 

  261. Paulsen H, von Deessen U, Tietz H (1985) ibid 137: 63

    CAS  Google Scholar 

  262. Paulsen H, Tietz H (1985) Angew Chem, Int Engl Ed 24: 128

    Google Scholar 

  263. Paulsen H, Tietz H (1985) Carbohydr Res 144: 205

    CAS  Google Scholar 

  264. Kitajima T, Sugimoto M, Nukada T, Ogawa T (1984) ibid 127: C1

    Google Scholar 

  265. Ogawa T, Sugimoto M, Kitajima T, Sadozai KK, Nukada T (1986) Tetrahedron Lett 27: 5739

    CAS  Google Scholar 

  266. Furuhata K, Anazawa K, Itoh M, Shitori Y, Ogura H (1986) Chem Pharm Bull 34: 2725

    CAS  Google Scholar 

  267. Kunz H, Waldmann H (1985) J Chem Soc, Chem Commun 638

    Google Scholar 

  268. Paquet F, Sinaÿ P (1984) Tetrahedron Lett 25: 3071

    CAS  Google Scholar 

  269. Ogawa T, Sugimoto M (1985) Carbohydr Res 135: C5

    Google Scholar 

  270. Ogawa T, Sugimoto M (1985) Carbohydr Res 135: C5

    Google Scholar 

  271. Sugimoto M, Ogawa T (1985) Glycoconjugate J 2: 5

    CAS  Google Scholar 

  272. Hirabayashi Y, Sugimoto M, Ogawa T, Matsumoto M, Tagawa M, Taniguchi M (1986) Biochim Biophys Acta 875: 126

    CAS  Google Scholar 

  273. Paulsen H, von Deessen U (1986) Carbohydr Res 146: 147

    CAS  Google Scholar 

  274. Sugimoto M, Numata M, Koike K, Nakahara Y, Ogawa T (1986) ibid 156: C1

    Google Scholar 

  275. Okamoto K, Kondo T, Goto T (1986) Tetrahedron Lett 27: 5229

    CAS  Google Scholar 

  276. Okamoto K, Kondo T, Goto T (1986) ibid 27: 5233

    CAS  Google Scholar 

  277. Okamoto K, Kondo T, Goto T (1986) Chem Lett 1449

    Google Scholar 

  278. Sabesan S, Paulson JC (1986) J Am Chem Soc 108: 2068

    CAS  Google Scholar 

  279. Thiem J, Treder W (1986) Angew Chem, Int Engl Ed 25: 1096

    Google Scholar 

  280. Neuenhofer S, Schwarzmann G, Egge H, Sandhoff K (1985) Biochemistry 24: 525

    CAS  Google Scholar 

  281. Acquotti D, Sonnino S, Masserini M, Casella L, Fronza G, Tettamanti G (1986) Chem Phys Lipids 40: 71

    CAS  Google Scholar 

  282. Gazzotti G, Sonnino S, Ghidoni R, Orlando P, Tettamanti G (1984) Glycoconjugate J 1: 111

    CAS  Google Scholar 

  283. Dorland L, Haverkamp J, Schauer R, Veldink GA, Vliegenthart JFG (1982) Biochem Biophys Res Commun 104: 1114

    CAS  Google Scholar 

  284. Brossmer R, Rose U, Kasper D, Smith TL, Grasmunk H, Unger FM (1980) ibid 96: 1282

    CAS  Google Scholar 

  285. Stepanov AE, Shvets VI (1979) Chem Phys Lipids 25: 247

    CAS  Google Scholar 

  286. Berridge MJ (1986) Biochem Soc Symposium 52: 153

    CAS  Google Scholar 

  287. Majerus PJ, Connolly TM, Deckmyn H, Ross TS, Bross TE, Ishii, H, Bansal VS, Wilson DB (1986) Science 234: 1519

    CAS  Google Scholar 

  288. Abdel-Latif AA (1986) Pharmacol Rev 38: 227

    CAS  Google Scholar 

  289. Parthasarathy R, Eisenberg F (1986) Biochem J 235: 313

    CAS  Google Scholar 

  290. Troyer DA, Schwertz DW, Kreisberg JI, Venkatachalam MA (1986) Annu Rev Physiol 48: 51

    CAS  Google Scholar 

  291. Irvine RF, Moor RM (1986) Biochem J 240: 917

    CAS  Google Scholar 

  292. Stepanov AE, Shvets VI, Evstigneeva RP (1977) Zhur Org Khim. 13: 1410 (1295)

    CAS  Google Scholar 

  293. Stepanov AE, Shvets VI, Evstigneeva RP (1977) Zhur obshchei Khim 47: 1653 (1515)

    CAS  Google Scholar 

  294. Sibrikov YI, Stepanov AE, Shvets VI (1981) Zhur Org Khim 17: 2015 (1799)

    CAS  Google Scholar 

  295. Letsinger RL, Miller PS (1969) J Am Chem Soc 91: 3356

    CAS  Google Scholar 

  296. Stepanov AE, Sibrikov YI, Shvets VI (1980) Zhur Org Khim 16: 2284 (1946)

    CAS  Google Scholar 

  297. Krylova VN, Lyutik AI, Kobelkova NN, Shvets VI, Evstigneeva RP (1978) ibid. 14: 1858 (1725)

    CAS  Google Scholar 

  298. Sibrikov YI, Stepanov AE, Shvets VI (1984) ibid 20: 979 (891)

    CAS  Google Scholar 

  299. Kaplun AP, Krylova VN, Soloveichik GY, Klyashchitskii BA, Shvets VI (1978) ibid 14: 1863 (1730)

    CAS  Google Scholar 

  300. Kaplun AP, Krylova VN, Soloveichik GY, Shvets VI (1979) ibid 15: 307 (266)

    CAS  Google Scholar 

  301. Garegg PJ, Lindberg B, Kvarnström I, Svensson SCT (1985) Carbohydr Res 139: 209

    CAS  Google Scholar 

  302. Krylova VN, Lyutvik AI, Kosaeva AE, Shvets VI (1979) Zhur. Org Khim 15: 2323 (2104)

    CAS  Google Scholar 

  303. Shvets VI, Sukhanov VA, Okhanov VV, Zhdanov RI (1979) Chem Phys Lipids 23: 163

    CAS  Google Scholar 

  304. Shragin AS, Kuzmina YV, Borin ML, Kaplun AP, Shvets VI (1985) Bioorg Khim 11: 1669

    CAS  Google Scholar 

  305. Krylova VN, Kobelkova NI, Oleinik GF, Shvets VI (1980) Zhur Org Khim 16: 62 (59)

    CAS  Google Scholar 

  306. Krylova VN, Gornaeva NP, Oleinik GF, Shvets VI (1980) ibid 16: 315 (277)

    CAS  Google Scholar 

  307. Krylova VN, Gornaeva NP, Shvets VI, Evstigneeva RP (1979) Dokl Akad Nauk SSSR 246: 339

    CAS  Google Scholar 

  308. Krylova VN, Lyutvik AI, Gornaeva NP, Shvets VI (1979) Zhur obshchei Khim 51: 210 (183)

    Google Scholar 

  309. Gigg J, Gigg R, Payne S, Conant R (1985) Carbohydr Res 142: 132

    CAS  Google Scholar 

  310. Gigg J, Gigg R, Payne S, Conant R (1985) ibid 140: C1

    Google Scholar 

  311. Ozaki S, Watanabe Y, Ogasawara T, Kondo Y, Shiotani N, Nishii H, Matsuki T (1986) Tetrahedron Lett 27: 3157

    CAS  Google Scholar 

  312. Hamblin MR, Potter BVL, Gigg R (1987) J Chem Soc, Chem Commun 626

    Google Scholar 

  313. Houslay MD (1987) Trends Biochem Sci 12: 1

    Google Scholar 

  314. Boutin RH, Rapoport H (1986) J Org Chem 51: 5320

    CAS  Google Scholar 

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  1. Laboratory of Lipid and General Chemistry, National Institute for Medical Research, Mill Hill, NW7 1AA, London, U.K.

    Jill Gigg & Roy Gigg

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  1. Jill Gigg
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Gigg, J., Gigg, R. (1990). Synthesis of glycolipids. In: Carbohydrate Chemistry. Topics in Current Chemistry, vol 154. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0111560

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