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C-Glycosylation

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Glycoscience

Abstract

This chapter deals with C‑glycosylation, a carbon--carbon bond-forming reaction at an anomeric carbon of carbohydrate and its derivatives. Since synthesis of natural products containing the C‑glycosidic linkage was one of the major issues in organic synthesis in the 1970s, extensive efforts have been devoted to developing stereoselective synthesis of C‑glycoside, which includes a variety of C–C bond formations by using anomeric cations (oxocarbenium cations), anomeric radicals, and anomeric anions, as well as sigmatropic rearrangement and transition metal‐catalyzed reactions. Among these reactions, useful C‑glycosylations with high stereoselectivities are reviewed in this chapter with an emphasis on the reaction mechanisms.

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Abbreviations

HMPA:

hexamethylphosphoramide

MCPBA:

m-chloroperoxybenzoic acid

TIPS:

triisopropylsilyl

TMSCN:

trimethylsilyl cyanide

References

  1. Frank RW, Tsuji M (2006) Acc Chem Res 39:692

    Article  Google Scholar 

  2. Okadaic acid: (a) Isobe M, Ichikawa Y, Bai DL, Masaki H, Goto T (1986) Tetrahedron 27:4767 and references cited therein; (b) Ley SV, Humphries AC, Eick H, Downham R, Ross AR, Boyce RJ, Pavey JBJ, Pietruszka J (1998) J Chem Soc Perkin Trans 1 3907; (c) Forsyth CJ, Sabes SF, Urbanek RA (1997) J Am Chem Soc 119:8381; Brevetoxin A: Nicolaou KC, Yang Z, Shi GQ, Gunzner JL, Agrios KA, Gärtner P (1998) Nature 392:264; Review of aryl-C‑glycosides: Jaramillo C, Knapp S (1994) Synthesis 1

    Google Scholar 

  3. Previous reviews on synthesis of C‑glycosides: (a) Postema MHD (1995) C‑Glycoside Synthesis. CRC Press, London; (b) Levy DE, Tang C (1995) The Chemistry of C‑Glycosides. Pergamon, Oxford; (c) Postema MHD (1992) Tetrahedron 48:8545; (d) Du Y, Linhardt RJ, Vlahov IR (1998) Tetrahedron 54:9913; (e) Meo P, Osborn HMI (2003) In: Osborn HMI (ed) Carbohydrate. Academic Press, Amsterdam p 337

    Google Scholar 

  4. (a) Rodrigues F, Canac Y, Lubineau A (2000) J Chem Soc Chem Commun 2049; (b) Bragnier N, Scherrmann MC (2005) Synthesis 814

    Google Scholar 

  5. Tatsuta K, Nakano S, Narazaki F, Nakamura Y (2001) Tetrahedron Lett 42:7625

    Article  CAS  Google Scholar 

  6. Harvey JE, Raw SA, Taylor RJK (2004) Org Lett 6:2611

    Article  CAS  Google Scholar 

  7. Review of exo-glycal: Taillefumier C, Chapleur Y (2004) Chem Rev 104:263

    Article  Google Scholar 

  8. (a) Schweizer F, Otter A, Hindsgaul O (2001) Synlett 1743; (b) Penner M, Taylor D, Desautels D, Marat K, Schweizer F (2005) Synlett 212

    Google Scholar 

  9. Trotter NS, Takahashi S, Nakata T (1999) Org Lett 1:957

    Article  CAS  Google Scholar 

  10. Tatsuta K, Mukai H, Takahashi M (2000) J Antibiotics 53:430

    CAS  Google Scholar 

  11. (a) Gascón-López M, Motevalli M, Paloumbis G, Bladon P, Wyatt PB (2003) Tetrahedron 59:0349; (b) Coumbarides GS, Motevalli M, Muse WA, Wyatt PB (2006) J Org Chem 71:7888

    Google Scholar 

  12. Molina A, Czernecki S, Xie J (1998) Tetrahedron Lett 39:7507

    Article  CAS  Google Scholar 

  13. (a) Lakhrissi M, Chapleur Y (1996) Angew Chem Int Ed 35:750; (b) Lakhrissi M, Taillefumier C, Lakhrissi M, Chapleur Y (2000) Tetrahedron Asymmetry 11:417

    Google Scholar 

  14. Taillefumier C, Lakhrissi Y, Lakhrissi M, Chapleur Y (2002) Tetrahedron Asymmetry 13:1707

    Article  CAS  Google Scholar 

  15. Lakhrissi M, Chapleur Y (1994) J Org Chem 59:5752

    Article  CAS  Google Scholar 

  16. Lakhrissi M, Chapleur Y (1998) Tetrahedron Lett 39:4659

    Article  CAS  Google Scholar 

  17. (a) RajanBabu TV, Reddy GS (1986) J Org Chem 51:5458; (b) Gómez AM, Pedregosa A, Valverde S, López JC (2003) Tetrahedron Lett 44:6111; (c) John BA, Pan YT, Elbein AD, Johnson CR (1997) J Am Chem Soc 119:4856; (d) Gueyrard D, Haddoub R, Salem A, Bacar NS, Goekjian PG (2005) Synlett 520

    Google Scholar 

  18. Alcaraz ML, Griffin FK, Paterson DE, Taylor RJK (1998) Tetrahedron Lett 39:8183

    Article  CAS  Google Scholar 

  19. (a) Yang WB, Yang YY, Gu YF, Wang SH, Chang CC, Lin CH (2002) J Org Chem 67:3773; (b) Terauchi M, Abe H, Matsuda A, Shuto S (2004) Org Lett 6:3751; (c) Lewis MD, Cha JK, Kishi Y (1982) J Am Chem Soc 104:4976; (d) Xie J, Durrat F, Valéry JM (2003) J Org Chem 68:7896; (e) Pulley SR, Carey JP (1998) J Org Chem 63:5275; (f) Lancelin JM, Zollo PHA, Sinaÿ P (1983) Tetrahedron Lett 24:4833; (g) Czernecki S, Ville G (1989) J Org Chem 54:610; (h) Ellsworth BA, Doyle AG, Patel M, Caceres‐Cortes J, Meng W, Deshpande PP, Pullockaran A, Washburn WN (2003) Tetrahedron Asymmetry 14:3243; (i) Labéguère F, Lavergne JP, Martinez J (2002) Tetrahedron Lett 43:7271; (j) Wellner E, Gustafsson T, Bäcklund J, Holmdahl R, Kihlberg J (2000) ChemBioChem 1:272; (k) Lowary T, Meldal M, Helmboldt A, Vasella A, Bock K (1998) J Org Chem 63:9657; (l) Dondoni A, Scherrmann MC (1994) J Org Chem 59:6404; (m) Nishikawa T, Koide Y, Kanakubo A, Yoshimura H, Isobe M (2006) Org Biomol Chem 4:1268

    Google Scholar 

  20. Review of thiazole as a nucleophile: Dondoni A, Marra A (1999) J Chem Soc Chem Commun 2133

    Google Scholar 

  21. Beignet J, Tiernan J, Woo CH, Kariuki BM, Cox LR (2004) J Org Chem 69:6341

    Article  CAS  Google Scholar 

  22. Terauchi M, Abe H, Matsuda A, Shuto S (2004) Org Lett 6:3751

    Article  CAS  Google Scholar 

  23. (a) Calzada E, Clarke CA, Roussin‐Bouchard C, Wightman RH (1995) J Chem Soc Perkin Trans 1 517; (b) Centrone CA, Lowary TL (2002) J Org Chem 67:8862; (c) Krohn K, Heins H, Wielckens K (1992) J Med Chem 35:511

    Google Scholar 

  24. (a) Boyd VA, Drake BE, Sulikowski GA (1993) J Org Chem 58:3191; (b) Kaelin DE Jr, Lopez OD, Martin SF (2001) J Am Chem Soc 123:6937

    Google Scholar 

  25. Uchiyama T, Woltering TJ, Wong W, Lin CC, Kajimoto T, Takebayashi M, Weitz-Schmidt G, Asakura T, Noda M, Wong CH (1996) Bioorg Med Chem 4:1149

    Article  CAS  Google Scholar 

  26. Kulkarni SS, Gervay-Hague J (2006) Org Lett 8:5765

    Article  CAS  Google Scholar 

  27. (a) Toshima K (2000) Carbohydr Res 327:15; (b) Yokoyama M, Toyoshima H, Shimizu M, Mito J, Togo H (1998) Synthesis 409

    Article  Google Scholar 

  28. (a) Nicolaou KC, Chucholowski A, Dolle RE, Randall JL (1984) J Chem Soc Chem Commun 1155; (b) Posner GH, Haines SR (1985) Tetrahedron Lett 26:1823

    Google Scholar 

  29. (a) Hosomi A, Sakata Y, Sakurai H (1984) Tetrahedron Lett 25:2383; Hosomi A, Sakata Y, Sakurai H (1987) Carbohydr Res 171:223; (b) Nicolaou KC, Dolle RE, Chucholowski A, Randall JL J Chem Soc Chem Commun (1984) 1153; (c) Giannis A, Sandhoff K (1985) 26:1479; (d) Palmacci ER, Seeberger PH (2001) Org Lett 3:1547; Plante OJ, Palmacci ER, Andrade RB, Seeberger PH (2001) J Am Chem Soc 123:9545; (e) Brenna E, Fuganti C, Grasselli P, Serra S, Zambotti S (2002) Chem Eur J 8:1872; (f) Fletcher S, Jorgensen MR, Miller AD (2004) Org Lett 6:4245

    Google Scholar 

  30. Hung SC, Lin CC, Wong CH (1997) Tetrahedron Lett 38:5419

    Article  CAS  Google Scholar 

  31. Allevi P, Anastasia M, Ciuffreda P, Fiecchi A, Scala A (1987) J Chem Soc Chem Commun 101

    Google Scholar 

  32. (a) Zhai D, Zhai W, Williams RM (1998) J Am Chem Soc 110:2501; (b) Jobron L, Leteux C, Veyrières A, Beau JM (1994) J Carbohydr Chem 13:507; Désiré J, Veyrières (1995) Carbohydr Res 268:177; (c) Nishikawa T, Ishikawa M, Isobe M (1999) Synlett 123; Nishikawa T, Koide Y, Kajii S, Wada K, Ishikawa M, Isobe M (2005) Org Biomol Chem 3:687; (d) Dondoni A, Mariotti G, Marra A (2002) J Org Chem 67:4475

    Google Scholar 

  33. (a) Isobe M, Nishizawa R, Hosokawa S, Nishikawa T (1998) J Chem Soc Chem Commun 2665; (b) Jiang Y, Isobe M (1996) Tetrahedron 52:2877; (c) Tsuboi K, Ichikawa Y, Isobe M (1997) Synlett 713; (d) Jiang Y, Ichikawa Y, Isobe M (1997) Tetrahedron 53:5103

    Google Scholar 

  34. Tamura S, Abe H, Matsuda A, Shuto S (2003) Angew Chem Int Ed 42:1021

    Article  Google Scholar 

  35. (a) Smith DM, Woerpel KA (2006) Org Biomol Chem 4:1195; (b) Larsen CH, Ridgway BH, Shaw JT, Smith DM, Woerpel KA (2005) J Am Chem Soc 127:10879

    Google Scholar 

  36. Brimble MA, Brenstrum TJ (2000) Tetrahedron Lett 41:2991

    Article  CAS  Google Scholar 

  37. Allevi P, Anastasia M, Ciuffreda P, Fiecchi A, Scala A, Bingham S, Muir M, Tyman J (1991) J Chem Soc Chem Commun 1319

    Google Scholar 

  38. Furuta T, Kimura T, Kondo S, Mihara H, Wakimoto T, Nukaya H, Tsuji K, Tanaka K (2004) Tetrahedron 60:9375

    Article  CAS  Google Scholar 

  39. (a) Kuribayashi T, Ohkawa N, Satoh S (1998) Tetrahedron Lett 39:4537; (b) Kuribayashi T, Mizuno Y, Gohya S, Satoh S (1999) J Carbohydr Chem 18:371

    Google Scholar 

  40. Matsuo G, Miki Y, Nakata M, Matsumura S, Toshima K (1999) J Org Chem 64:7101

    Article  CAS  Google Scholar 

  41. Matsumoto T, Katsuki M, Suzuki K (1988) Tetrahedron Lett 29:6935

    Article  CAS  Google Scholar 

  42. Ben A, Yamauchi T, Matsumoto T, Suzuki K (2004) Synlett 225

    Google Scholar 

  43. Futagami S, Ohashi Y, Imura K, Hosoya T, Ohmori K, Matsumoto T, Suzuki K (2000) Tetrahedron Lett 41:1063

    Article  CAS  Google Scholar 

  44. Thorn SN, Gallagher T (1996) Synlett 185

    Google Scholar 

  45. Thorn SN, Gallagher T (1996) Synlett 856

    Google Scholar 

  46. Cook MJ, Fletcher MJE, Gray D, Lovell PJ, Gallagher T (2004) Tetrahedron 60:5085

    Article  CAS  Google Scholar 

  47. Steinhuebel DP, Fleming JJ, Du Bois J (2002) Org Lett 4:293

    Article  CAS  Google Scholar 

  48. (a) Bussolo VD, Caselli M, Romano MR, Pineschi M, Crotti P (2004) J Org Chem 69:7383; (b) Bussolo VD, Caselli M, Romano R, Pineschi M, Crotti P (2004) J Org Chem 69:8702

    Google Scholar 

  49. Saeeng R, Isobe M (2006) Chem Lett Highlight Rev 35:552

    Article  CAS  Google Scholar 

  50. (a) Danishefsky SJ, Kerwin JF Jr (1982) J Org Chem 47:3805; (b) Takhi M, Rahman AA-HA, Schmidt RR (2001) Tetrahedron Lett 42:4053; (c) Zhu YH, Vogel P (2001) Synlett 82; (d) Yadav JS, Reddy BVS, Rao CV, Chand PK, Prasad AR (2001) Synlett 1638; (e) Tsukiyama T, Isobe M (1992) Tetrahedron Lett 33:7911; (f) Saeeng R, Sirion U, Sahakitpichan P, Isobe M (2003) Tetrahedron Lett 44:6211; (g) Saeeng R, Isobe M (2005) Org Lett 7:1585; (h) Isobe M, Saeeng R, Nishizawa R, Konobe M, Nishikawa T (1999) Chem Lett 467

    Google Scholar 

  51. (a) Hosokawa S, Kirschbaum B, Isobe M (1998) Tetrahedron Lett 39:1917; (b) Das SK, Reddy KA, Abbineni C, Roy J, Rao KVLN, Sachwani RH, Iqbal J (2003) Tetrahedron Lett 44:4507; (c) Shoji M, Akiyama N, Tsubone K, Lash LL, Sanders JM, Swanson GT, Sakai R, Shimamoto K, Oikawa M, Sasaki M (2006) J Org Chem 71:5201

    Google Scholar 

  52. Tanaka S, Tsukiyama T, Isobe M (1993) Tetrahedron Lett 34:5757

    Article  CAS  Google Scholar 

  53. Hosokawa S, Isobe M (1998) Tetrahedron Lett 39:2609

    Article  CAS  Google Scholar 

  54. Hosokawa S, Isobe M (1999) J Org Chem 64:37

    Article  CAS  Google Scholar 

  55. Pulley SR, Carey JP (1998) J Org Chem 63:5257

    Article  Google Scholar 

  56. (a) Allwein SP, Cox JM, Howard BE, Johnson HWB, Rainier JD (2002) Tetrahedron 58:1997; (b) Rainier JD, Cox JM (2000) Org Lett 2:2707; (c) Evans DA, Trotter BW, Côté B (1998) Tetrahedron Lett 39:1709; (d) Timmers CM, Dekker M, Buijsman RC, van der Marel GA, Ethell B, Burchell AB, Mulder GJ, van Boom JH (1997) Bioorg Med Chem Lett 7:1501; (e) Leeuwenburgh MA, van der Marel GA, Overkleeft HS, van Boom JH (2003) J Carbohydr Chem 22:549; (f) Wipf P, Pierce JG, Zhuang N (2005) Org Lett 7:483

    Google Scholar 

  57. Hayward MM, Roth RM, Duffy KJ, Dalko PI, Stevens KL, Guo J, Kishi Y (1998) Angew Chem Int Ed 37:192

    Article  CAS  Google Scholar 

  58. Evans DA, Trotter BW, Coleman PJ, Côté B, Dias LC, Rajapakse HA, Taylor AN (1999) Tetrahedron 55:8671

    Article  CAS  Google Scholar 

  59. Manabe S, Marui Y, Ito Y (2003) Chem Eur J 9:1435

    Article  Google Scholar 

  60. Stichler‐Bonaparte J, Vasella A (2001) Helv Chim Acta 84:2355

    Article  Google Scholar 

  61. Stichler‐Bonaparte J, Bernet B, Vasella A (2002) Helv Chim Acta 85:2235

    Article  Google Scholar 

  62. Jaouen V, Jégou A, Veyrières A (1996) Synlett 1218

    Google Scholar 

  63. Review: Togo h, He W, Waki Y, Yokoyama M (1998) Synlett 700

    Google Scholar 

  64. Giese B (1989) Angew Chem Int Ed 28:969

    Article  Google Scholar 

  65. Abe H, Shuto S, Matsuda A (2001) J Am Chem Soc 123:11870

    Article  CAS  Google Scholar 

  66. (a) Giese B, Linker T, Muhn R (1989) Tetrahedron 45:935; Giese B, Dupuis J (1983) Angew Chem Int Ed 22:622; Giese B, Dupuis J, Nix M (1987) Org Synth 65:236; Giese B, Dupuis J, Leising M, Nix M, Lindner HJ (1987) Carbohydr Res 171:329; (b) Harenbrock M, Matzeit A, Schäfer HJ (1996) Liebigs Ann Chem 55; (c) Keck GE, Enholm EJ, Yates JB, Wiley MR (1985) Tetrahedron 41:4079; (d) Krishna PR, Lavanya B, Jyothi Y, Sharma GVM (2003) J Carbohydr Chem 22:423; (e) Kessler H, Wittmann V, Köck M, Kottenhahn M (1992) Angew Chem Int Ed 31:902; (f) Pontén F, Magnusson G (1996) J Org Chem 61:7463; (g) Junker HD, Phung N, Fessner WD (1999) Tetrahedron Lett 40:7063

    Google Scholar 

  67. (a) Bouvet VR, Ben RN (2006) J Org Chem 71:3619; (b) Roe BA, Boojamra CG, Griggs JL, Bertozzi CR (1996) J Org Chem 61:6442; (c) Grant L, Liu Y, Walsh KE, Walter DS, Gallagher T (2002) Org Lett 4:4623; (d) SanMartin R, Tavassoli B, Walsh KE, Walter DS, Gallagher T (2000) Org Lett 2:4051; (e) Abel S, Linker T, Giese B (1991) Synlett 171

    Google Scholar 

  68. (a) Giese B, Hoch M, Lamberth C, Schmidt RR (1988) Tetrahedron Lett 29:1375; (b) Pasquarello C, Demange R, Vogel P (1999) Bioorg Med Chem Lett 9:793

    Google Scholar 

  69. (a) Paulsen H, Matschulat P (1991) Liebigs Ann Chem 487; (b) Nagy JO, Bednarski MD (1991) Tetrahedron Lett 32:3953

    Google Scholar 

  70. Bois M, Skrydstrup T (1995) Chem Rev 95:1253

    Article  Google Scholar 

  71. Stork G, Suh HS, Kim G (1991) J Am Chem Soc 113:7054

    Article  CAS  Google Scholar 

  72. Mazéas D, Skrydstrup T, Doumeix O, Beau JM (1994) Angew Chem Int Ed 33:1383

    Article  Google Scholar 

  73. (a) Zhang J, Clive DLJ (1999) J Org Chem 64:770; (b) Zhang J, Clive DLJ (1999) J Org Chem 64:1754

    Google Scholar 

  74. Review: (a) Somsák L (2001) Chem Rev 101:81; (b) Beau JM, Gallagher T (1997) In Topics in Current Chemistry 187:1. Springer, Berlin Heidelberg New York

    Google Scholar 

  75. (a) Hoffmann M, Kessler H (1994) Tetrahedron Lett 35:6067; (b) Burkhart F, Kessler H (1998) Tetrahedron Lett 39:255

    Google Scholar 

  76. (a) Lieberknecht A, Griesser H, Krämer B, Bravo RD, Colinas PA, Grigera RJ (1999) Tetrahedron 55:6475; (b) Colinas PA, Ponzinibbio A, Lieberknecht A, Bravo RD (2003) Tetrahedron Lett 44:7985

    Google Scholar 

  77. (a) Lesimple P, Beau JM, Jaurand G, Sinaÿ P (1986) Tetrahedron Lett 27:6201; (b) Hanessian S, Martin M, Desai RC (1986) J Chem Soc Chem Commun 926

    Google Scholar 

  78. Parker KA, Su DS (2005) J Carbohydr Chem 24:199

    Article  CAS  Google Scholar 

  79. (a) Griffin FK, Murphy PV, Paterson DE, Taylor RJK (1998) Tetrahedron Lett 39:8179; (b) Belica PS, Franck RW (1998) Tetrahedron Lett 39:8225

    Google Scholar 

  80. Griffin FK, Paterson DE, Murphy PV, Taylor RJK (2002) Eur J Org Chem 1305

    Google Scholar 

  81. Skrydstrup T, Jarreton O, Mazéas D, Urban D, Beau JM (1998) Chem Eur J 4:655

    Article  CAS  Google Scholar 

  82. Hung SH, Wong CH (1996) Angew Chem Int Ed 35:2671

    Article  CAS  Google Scholar 

  83. (a) Andersen L, Mikkelsen LM, Beau JM, Skrydstrup T (1998) Synlett 139; (b) Urban D, Skrydstrup T, Beau JM (1998) J Org Chem 63:2507

    Google Scholar 

  84. Urban D, Skrydstrup T, Beau JM (1998) J Chem Soc Chem Commun 955

    Google Scholar 

  85. (a) Du Y, Linhardt RJ (1998) Carbohydr Res 308:161; (b) Polat T, Du Y, Linhardt RJ (1998) Synlett 1195; (c) Malapelle A, Abdallah Z, Doisneau G, Beau JM (2006) Angew Chem Int Ed 45:6016

    Google Scholar 

  86. (a) Bazin HG, Du Y, Polat T, Linhardt RJ (1999) J Org Chem 64:7254; (b) Abdallah Z, Doisneau G, Beau JM (2003) Angew Chem Int Ed 42:5209

    Google Scholar 

  87. Fraser-Reid B, Dawe RD, Tulshian DB (1979) Can J Chem 57:1746

    Article  CAS  Google Scholar 

  88. Ireland RE, Wilcox CS, Thaisrivongs S, Vanier NR (1979) Can J Chem 57:1743

    Article  CAS  Google Scholar 

  89. Ireland RE, Anderson RC, Badoud R, Fitzsimmons BJ, McGarvey GJ, Thaisrivongs S, Wilcox CS (1983) J Am Chem Soc 105:1988

    Article  CAS  Google Scholar 

  90. Colombo L, Di Giacomo M, Ciceri P (2002) Tetrahedron 58:9381

    Article  CAS  Google Scholar 

  91. (a) Godage HY, Fairbanks AJ (2000) Tetrahedron Lett 41:7589; (b) Chambers DJ, Evans GR, Fairbanks AJ (2005) Tetrahedron Asymmetry 16:45

    Google Scholar 

  92. Tulshian DB, Fraiser-Reid B (1984) J Org Chem 49:518

    Article  CAS  Google Scholar 

  93. (a) Tomooka K, Kikuchi M, Igawa K, Keong PH, Nakai T (1999) Tetrahedron Lett 40:1917; (b) Tomooka K, Kikuchi M, Igawa K, Suzuki M, Keong PH, Nakai T (2000) Angew Chem Int Ed 39:4502

    Google Scholar 

  94. (a) Dunkerton LV, Serino AJ (1982) J Org Chem 47:2814; (b) Moineau C, Bolitt V, Sinou D (1998) J Org Chem 63:582

    Google Scholar 

  95. RajanBabu TV (1985) J Org Chem 50:3642

    Article  CAS  Google Scholar 

  96. Daves GD Jr (1990) Acc Chem Res 23:201

    Article  CAS  Google Scholar 

  97. Hsieh HP, McLaughlin LW (1995) J Org Chem 60:5356

    Article  CAS  Google Scholar 

  98. Friesen RW (2001) J Chem Soc Perkin Trans 1 1969

    Google Scholar 

  99. Friesen RW, Sturino CF (1990) J Org Chem 55:5808

    Article  CAS  Google Scholar 

  100. Boucard V, Larrieu K, Lubin-Germain N, Uziel J, Auge J (2003) Synlett 1834

    Google Scholar 

  101. Tius MA, Gu XQ, Gomez-Galeno J (1990) J Am Chem Soc 112:8188

    Article  CAS  Google Scholar 

  102. Nicolaou KC, Shi GQ, Gunzner L, Gärtner P, Yang Z (1997) J Am Chem Soc 119:5467

    Article  CAS  Google Scholar 

  103. Kadota I, Takamura H, Nishii H, Yamamoto Y (2005) J Am Chem Soc 127:9246

    Article  CAS  Google Scholar 

  104. Gong H, Sinisi R, Gagné MR (2007) J Am Chem Soc 129:1908

    Article  CAS  Google Scholar 

  105. Potuzak JS, Tan DS (2004) Tetrahedron Lett 45:1797

    Article  CAS  Google Scholar 

  106. Sasaki M, Fuwa H, Ishikawa M, Tachibana K (1999) Org Lett 1:1075

    Article  CAS  Google Scholar 

  107. Chatani N, Ikeda T, Sano T, Sonoda N, Kurosawa H, Kawasaki Y, Murai S (1988) J Org Chem 53:3387

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Graduate School of Bioagricultural Sciences, Nagoya University, 464-8601, Nagoya, Japan

    Toshio Nishikawa, Masaatsu Adachi & Minoru Isobe

Authors
  1. Toshio Nishikawa
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  2. Masaatsu Adachi
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  3. Minoru Isobe
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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.

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Nishikawa, T., Adachi, M., Isobe, M. (2008). C-Glycosylation. In: Fraser-Reid, B.O., Tatsuta, K., Thiem, J. (eds) Glycoscience. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-30429-6_17

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