Skip to main content
SpringerLink
Log in
Book cover

Glycoscience pp 227–269Cite as

Heteroatom Exchange

  • Reference work entry

  • 8758 Accesses

Abstract

Saccharides derived with a variety of functional groups are usually of great importance in many biological and chemical aspects. The chemical modifications of saccharides with heteroatoms at nonanomeric positions are reviewed in this chapter.

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   1,199.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD   549.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Abbreviations

AIBN:

azo-bis-isobutyronitrile

CAN:

ceric ammonium nitrate

DAST:

diethylaminosulfur trifluoride

DBU:

1,8-diazabicyclo[5.4.0]undec-7-ene

DEAD:

diethyl azodicarboxylate

DFMBA:

N,N‐diethyl‐α,α‐difluoro‐(m‐methylbenzyl)amine

DIAD:

diisopropyl azodicarboxylate

dppb:

1,4-bis(diphenylphosphino)butane

IDCP:

iodonium di‐sym‐collidine perchlorate

IBX:

1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide

NBS:

N-bromosuccinimide

PMB:

p-methoxybenzyl

SMDA:

sodium dihydrobis(2‑methoxyethoxy)aluminate

TASF:

tri(dimethylamino)-sulfonium difluorotrimethylsilicate

TFAA:

trifluoroacetic anhydride

References

  1. Hanessian S (1997) Selected reactions in carbohydrate chemistry. In: Hanessian S (ed) Preparative carbohydrate chemistry. Dekker, New York, p 85

    Google Scholar 

  2. Boons GJ (2000) Functionalised saccharides. In: Boons GJ, Hale KJ (eds) Organic synthesis with carbohydrates. Sheffield Academic Press, Sheffield, p 56

    Google Scholar 

  3. Szarek WA (1973) Adv Carbohydr Chem Biochem 28:250

    Google Scholar 

  4. Szarek WA (1973) Adv Carbohydr Chem Biochem 28:230

    Google Scholar 

  5. Card PJ (1985) J Carbohydr Chem 4:451

    CAS  Google Scholar 

  6. Wu MC, Anderson L, Slife TW, Jensen LJ (1974) J Org Chem 39:3014

    CAS  Google Scholar 

  7. Hanessian S, Vatèle JM (1981) Tetrahedron Lett 22:3579

    CAS  Google Scholar 

  8. Nadkarni S, Williams NR (1965) J Chem Soc 3496

    Google Scholar 

  9. Capon B (1969) Chem Rev 69:407

    CAS  Google Scholar 

  10. Brimacombe JS, Doner LW, Rollins AJ (1972) J Chem Soc Perkin Trans 1 2977

    Google Scholar 

  11. Brimacombe JS, Doner LW, Rollins AJ (1973) J Chem Soc Perkin Trans 1 1295

    Google Scholar 

  12. Buss DH, Hough L, Richardson AC (1963) J Chem Soc 5295

    Google Scholar 

  13. Zu Reckendorf WM, Bonner WA (1963) Tetrahedron 19:1711

    CAS  Google Scholar 

  14. Binkley RW, Hehemann DG (1979) Adv Carbohydr Chem 24:139

    Google Scholar 

  15. Vox JN, Van Boom JH, Van Boechel CAA, Beetz T (1984) 3:117

    Google Scholar 

  16. Richardson AC (1969) Carbohydr Res 10:395

    CAS  Google Scholar 

  17. Gnichtel H, Rebentisch D, Tompkins TC, Gross PH (1982) J Org Chem 47:2691

    Google Scholar 

  18. Wright JA, Taylor NF (1966–1967) Carbohydr Res 3:333

    Google Scholar 

  19. Buchanan JG, Schwarz JCP (1962) J Chem Soc 4770

    Google Scholar 

  20. Guthrie RD, Williams GJ (1976) J Chem Soc Perkin Trans 1 801

    Google Scholar 

  21. Christensen JE, Goodman L (1961) J Am Chem Soc 83:3827

    CAS  Google Scholar 

  22. Van Der Klein PAM, Filemon W, Veeneman GH, Van Der Marel GA, Van Boom JH (1992) J Carbohydr Chem 11:837

    Google Scholar 

  23. Hanessian S, Pleassas NR (1969) J Org Chem 34:1035, 1045 and 1053

    CAS  Google Scholar 

  24. Ferier RJ, Prasad N (1969) J Chem Soc 570

    Google Scholar 

  25. Ferier RJ, Ponpipom MJ (1971) J Chem Soc Chem Commun 553

    Google Scholar 

  26. Leblanc Y, Fitzsimmons BJ, Springer JP, Rokach J (1989) J Am Chem Soc 111:2995

    CAS  Google Scholar 

  27. Dios A, Geer A, Marzabadi CH, Franck RM (1998) J Org Chem 63:6673

    CAS  Google Scholar 

  28. Dahl RS, Finney NS (2004) J Am Chem Soc 126:8356

    CAS  Google Scholar 

  29. Giese B (1986) Radical in organic synthesis: Formation of carbon‐carbon bonds. Pergamon Press, Oxford

    Google Scholar 

  30. Taylor NF (1988) Fluorinated carbohydrate. Chemical and biological aspects, ACS Symp Ser 374

    Google Scholar 

  31. Beuthien-Baumann B, Hamacher K, Oberdorfer F, Steinbach J (2000) Carbohydr Res 327:107

    CAS  Google Scholar 

  32. Tomas SS, Plenkiewicz J, Ison ER, Bols M, Zou W, Szarek WA, Kisilevsky R (1995) Biochim Biophys Acta 1272:37

    Google Scholar 

  33. Suami T, Hough L, Tsuboi M, Machinami T, Watanabe N (1994) J Carbohydr Chem 13:1079

    CAS  Google Scholar 

  34. Szarek WA (1973) Adv Carbohydr Chem Biochem 28:225

    CAS  Google Scholar 

  35. Su TL, Klein RS, Fox JJ (1982) J Org Chem 47:1506

    CAS  Google Scholar 

  36. Hamacher K, Coenen HH, Stocklin G (1986) J Nucl Med 27:235

    CAS  Google Scholar 

  37. Tsuchiya T, Takahashi Y, Endo M, Umezawa S, Umezawa H (1985) J Carbohydr Chem 4:587

    CAS  Google Scholar 

  38. Haradahira T, Maeda M, Kai Y, Omae H. Kojima M (1985) Chem Pharm Bull 33:165

    CAS  Google Scholar 

  39. Doboszewski B, Hay GW, Szarek WA (1987) Can J Chem 65:412

    CAS  Google Scholar 

  40. Anisuzzaman AKM, Whistler RL (1978) Carbohydr Res 61:511

    CAS  Google Scholar 

  41. Whistler RL, Anisuzzaman AKM (1980) Methods Carbohydr Chem 8:227

    CAS  Google Scholar 

  42. Haylock CR, Melton LD, Slessor KN, Tracey AS (1971) Carbohydr Res 16:375

    CAS  Google Scholar 

  43. Hanessian S, Ponpidom MM, Lavallee P (1972) Carbohydr Res 24:45

    CAS  Google Scholar 

  44. Garegg PJ, Samuelsson B (1980) J Chem Soc Perkin Trans 1 2866

    Google Scholar 

  45. Abram TS, Baker R, Exon CM (1982) J Chem Soc Perkin Trans 1 285

    Google Scholar 

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

    CAS  Google Scholar 

  47. Kielberg J, Frejd T, Jansson K, Sundin A, Magnusson G (1988) Carbohydr Res 176:271

    Google Scholar 

  48. Mitsunobu S (1981) Synthesis 1

    Google Scholar 

  49. Hannelore V, Brandstetter H, Zbiral E (1980) Helv Chim Acta 63:327

    Google Scholar 

  50. Verheyden JPH, Moffatt JG (1970) J Org Chem 35:2319

    CAS  Google Scholar 

  51. Hanessian S, Plessas NR (1969) J Org Chem 34:2163

    CAS  Google Scholar 

  52. Back TG, Barton DHR, Rao BL (1977) J Chem Soc Perkin Trans 1 1715

    Google Scholar 

  53. Hanessian S (1968) Adv Chem Ser 74:159

    Google Scholar 

  54. Bragg PD, Jones JKN, Turner JC (1959) Can J Chem 37:1412

    CAS  Google Scholar 

  55. Jones JKN, Perry MB, Turner JC (1960) Can J Chem 38:1122

    CAS  Google Scholar 

  56. Jennings HJ, Jones JKN (1963) Can J Chem 41:1151

    CAS  Google Scholar 

  57. Jennings HJ, Jones JKN (1965) Can J Chem 43:2372

    CAS  Google Scholar 

  58. Jennings HJ (1970) Can J Chem 48:1834

    CAS  Google Scholar 

  59. Jennings HJ, Jones JKN (1965) Can J Chem 43:3018

    CAS  Google Scholar 

  60. An SH, Bobek M (1986) Tetrahedron Lett 27:3219

    CAS  Google Scholar 

  61. Card PJ (1983) J Org Chem 48:393

    CAS  Google Scholar 

  62. Card PJ (1985) J Carbohydr Chem 4:453

    Google Scholar 

  63. Kobayashi S, Yoneda A, Fukuhara T, Hara S (2004) Tetrahedron Lett 45:1287

    CAS  Google Scholar 

  64. Penglis AAE (1981) Adv Carbohydr Chem Biochem 38:195

    CAS  Google Scholar 

  65. Tsuchiya T (1990) Adv Carbohydr Chem Biochem 48:91

    CAS  Google Scholar 

  66. Hartman MCT, Coward JK (2002) J Am Chem Soc 124:10036

    CAS  Google Scholar 

  67. Patroni JJ, Stick RV (1987) Aust J Chem 40:795

    CAS  Google Scholar 

  68. Fuentes J, Andulo M, Pradera MA (1998) Tetrahedron Lett 39:7149

    CAS  Google Scholar 

  69. Fuentes J, Andulo M, Pradera MA (1999) Carbohydr Res 319:192

    CAS  Google Scholar 

  70. Chana JS, Collins PN, Farnia F, Peacock DJ (1988) J Chem Soc Chem Commun 94

    Google Scholar 

  71. Ido T, Wan CN, Fowler JS, Wolf AP (1977) J Org Chem 42:2341

    CAS  Google Scholar 

  72. Korytnyk W, Petrieó CR (1982) Tetrahedron 38:2547

    CAS  Google Scholar 

  73. Thiem J, Klaffke W (1992) Top Curr Chem 154:285

    Google Scholar 

  74. Horton D, Priebe W, Snaidman M (1990) Carbohydr Res 205:71

    CAS  Google Scholar 

  75. Lafont D, Descotes G (1987) Carbohydr Res 166:195

    CAS  Google Scholar 

  76. Rawal GK, Rani S, Madhusudanan KP, Vankar YD (2007) Synthesis 2:294

    Google Scholar 

  77. Mc Carter JD, Adam MJ, Wihters SG (1995) Carbohydr Res 266:273

    CAS  Google Scholar 

  78. Ansell MF (1983) Rodd's chemistry of carbon compounds, vol 1F, G Supplement. Elsevier, Amsterdam

    Google Scholar 

  79. Blattner R, Ferrier RJ (1980) J Chem Soc Perkin Trans 1 1523

    Google Scholar 

  80. Ferrier RJ, Haines SR, Gainsford GJ, Gabe EJ (1984) J Chem Soc Perkin Trans 1 1683

    Google Scholar 

  81. Karpeisiuk W, Banaszek A, Zamojski A (1989) Carbohydr Res 186:156

    Google Scholar 

  82. Kloosterman M, Westerduin P, Van Boom JH (1986) Recl Trav Chim Pays-Bas 105:136

    CAS  Google Scholar 

  83. Viand MC, Rollin P (1990) Synthesis 130

    Google Scholar 

  84. Knapp S, Kukkola PJ, Sharma S, Murali Dhar TG, Naughton ABJ (1990) J Org Chem 55:5700

    CAS  Google Scholar 

  85. De Oliveira RN, Cottier L, Sinou D, Srivastava RM (2005) Tetrahedron 61:8271

    Google Scholar 

  86. Williams NR (1970) Adv Carbohydr Chem Biochem 25:109

    CAS  Google Scholar 

  87. Lemieux RU, James K, Nagabhushan TL (1973) Can J Chem 51:48

    CAS  Google Scholar 

  88. Lemieux RU, Ratcliffe M (1979) Can J Chem 57:1244

    CAS  Google Scholar 

  89. Czernecki S, Ayadi E, Randriamandimby D (1994) J Org Chem 59:8256

    CAS  Google Scholar 

  90. Griffith DA, Danishefsky SJ (1990) J Am Chem Soc 112:5811

    CAS  Google Scholar 

  91. Du Bois J, Tomooka CS, Hong J, Carreira EM (1997) J Am Chem Soc 119:3179

    CAS  Google Scholar 

  92. Dyong I, Schilte G, Lam-Chi Q, Friege H (1979) Carbohydr Res 68:257

    CAS  Google Scholar 

  93. Ravindran B, Sakthivel K, Suresh CG, Pathak T (2000) J Org Chem 65:2637

    CAS  Google Scholar 

  94. Nicolaou KC, Baran PS, Zhong YL, Vega JA (2000) Angew Chem 112:2625

    Google Scholar 

  95. Paul HW, Fraser-Reid B (1986) Carbohydr Res 150:111

    Google Scholar 

  96. Baer HH (1972) Methods Carbohydr Chem 6:245

    CAS  Google Scholar 

  97. Guthrie RD, Johnson LF (1961) J Chem Soc 4166

    Google Scholar 

  98. Lemieux RU, James K, Nagabhushan TL, Ito Y (1973) Can J Chem 51:33

    CAS  Google Scholar 

  99. Pelyvas I, Hasegawa A, Whistler RL (1986) Carbohydr Res 146:193

    CAS  Google Scholar 

  100. Montero A, Mann E, Herradón B (2005) Tetrahedron Lett 46:401

    CAS  Google Scholar 

  101. Nicolaou KC, Ladduwahetty T, Randall JL, Chucholowski A (1986) J Am Chem Soc 108:2466

    CAS  Google Scholar 

  102. Piispanen PS, Norin T (2003) J Org Chem 68:628

    CAS  Google Scholar 

  103. Brossmer R (1962) Methods Carbohydr Chem 1:216

    CAS  Google Scholar 

  104. Trimnell D, Stout EI, Doane WM, Russel CR (1975) J Org Chem 40:1337

    CAS  Google Scholar 

  105. Yu B, Zhu X, Hui Y (2001) Tetrahedron 57:9403

    CAS  Google Scholar 

  106. Arela O, Cicero D, De Lederkremer RM (1989) J Org Chem 54:1884

    Google Scholar 

  107. Dabbkowski W, Michalska, M, Tworowska I (1998) J Chem Soc Chem Commun 427

    Google Scholar 

  108. von Itzstein M, Jenkins MJ, Mocerino M (1990) Carbohydr Res 208:287

    Google Scholar 

  109. Whistler RL, Lake WC (1972) Methods Carbohydr Chem 6:286

    CAS  Google Scholar 

  110. Igarashi K, Honma T (1970) J Org Chem 35:606

    CAS  Google Scholar 

  111. Matsuura K, Maeda S, Araki Y, Ishido Y (1970) Tetrahedron Lett 2869

    Google Scholar 

  112. Kaye A, Neidle S, Reese CB (1988) Tetrahedron Lett 29:2711

    CAS  Google Scholar 

  113. Nicolaou KC, Mitchell HJ, Fylaktakidou KC, Suzuki H, Rodríguez RM (2000) Angew Chem Int Ed 39:1089

    CAS  Google Scholar 

  114. Zuurmond HM, Van Deklein PAM, Van Der Marel GA, Van Boom JH (1993) Tetrahedron 49:6501

    CAS  Google Scholar 

  115. Yu B, Yang Z (2001) Org Lett 3:377

    CAS  Google Scholar 

  116. Veselý J, Rohlenová A, Džoganová M, Trnka T, Tišlerová I, Šaman D, Ledvina M (2006) Synthesis 4:699

    Google Scholar 

  117. Santoyo‐Gonzales F, Garcia-Calvo-Flores F, Isaac-Garcia J, Hernandez-mateo P, Garcia‐mendoza P, Robles-Diaz R (1994) Tetrahedron 50:2877

    Google Scholar 

  118. Somask L, Ferrier RJ (1991) Adv Carbohydr Chem Biochem 49:37

    Google Scholar 

  119. Herdewijn PAM, Van Aerschot A, Jie L, Esmans E, Peneau‐Dupont J, Declerc JP (1991) J Chem Soc Perkin Trans 1 1729

    Google Scholar 

  120. Faure A, Kryczka B, Descotes G (1979) Carbohydr Res 74:127

    CAS  Google Scholar 

  121. Karpiesiuk W, Banaszek A (1994) Tetrahedron 50:2965

    CAS  Google Scholar 

  122. Seo K, Inokawa S (1970) Bull Chem Soc Jpn 43:3224

    Google Scholar 

  123. Seo K, Inokawa S (1975) Bull Chem Soc Jpn 48:1237

    CAS  Google Scholar 

  124. Hall LD, Steiner PR (1971) J Chem Soc Chem Commun 84

    Google Scholar 

  125. Brown MA, Cox PJ, Howie RA, Melvin OA, Taylor OJ, Wardell JL (1995) J Organomet Chem 498:275

    CAS  Google Scholar 

  126. Pàmies O, Diéguez M, Net G, Ruiz A, Claver C (2001) J Org Chem 66:8364

    Google Scholar 

  127. Nifant'ev EE, Gudkova IP, Kochetkov NK (1970) J Gen Chem USSR 40:425

    Google Scholar 

  128. Paulson H, Greve W (1973) Chem Ber 106:2124

    Google Scholar 

  129. Hanaya T, Yamamoto H (2002) Helv Chim Acta 85:2608

    CAS  Google Scholar 

  130. Yamashita M, Yoshikane M, Ogawa T, Inokawa S (1979) Tetrahedron 35:741

    CAS  Google Scholar 

  131. Paulson H, Greve W (1973) Chem Ber 106:2114

    Google Scholar 

  132. Takayanagi H, Yamashita M, Seo K, Yoshida H, Ogata T, Inokawa S (1974) Carbohydr Res 38:C19

    CAS  Google Scholar 

  133. Leonelli F, Capuzzi M, Calcagno V, Passacantilli P, Piancatelli G (2005) Eur J Org Chem 2671

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. The State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd #38, Beijing, 100083, China

    Yuhang Wang & Xin-Shan Ye

Authors
  1. Yuhang Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xin-Shan Ye
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Natural Products and Glycotechnology Research Institute Inc., North Caroline State University, 4118 Swarthmore Road, Durham, NC, 27707, USA

    Bertram O. Fraser-Reid Prof. Dr.

  2. University Graduate School of Science and Engineering, 3-4-1 Ohkubo, Shinjuku, Tokyo, Japan

    Kuniaki Tatsuta Prof. Dr.

  3. Faculty of ScienceDepartment of Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany

    Joachim Thiem Prof. Dr.

Rights and permissions

Reprints and permissions

Copyright information

© 2008 Springer-Verlag Berlin Heidelberg New York

About this entry

Cite this entry

Wang, Y., Ye, XS. (2008). Heteroatom Exchange. In: Fraser-Reid, B.O., Tatsuta, K., Thiem, J. (eds) Glycoscience. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-30429-6_5

Download citation

Publish with us

Policies and ethics

Search

Navigation