Synthesis of C-glycosides of biological interest

  • Francesco Nicotra
Chapter
First Online:
Part of the Topics in Current Chemistry book series (volume 187)

Abstract

This review article deals with C-glycosides, their biological interest and the synthetic methods for their preparation. C-Glycosides are carbohydrate analogs in which a carbon atom substitutes the oxygen involved in the glycosidic linkage. This modification compromises the anomeric reactivity of the sugar, giving rise to antimetabolites that can inhibit carbohydrate processing enzymes. The synthesis of C-glycosides can be performed from natural sugars, or from non-carbohydrate chiral starting materials. In the first case, the most common, the electrophilic character of the anomeric carbon is in general exploited, in reactions with proper carbon-nucleophiles. In this review, the different C-glycosylation procedures will be classified, and the stereochemical outcome of the reactions highlighted and explained. Particular attention will be paid to the uneasy syntheses of C-glycosides of aminosugars and of non-reducing disaccharides, and to the syntheses of C-glycosides of specific biological interest, such as the phosphono analogs of glycosyl phosphates.

Keywords

Biological Interest Anomeric Carbon Stable Analog Arbuzov Reaction Stereochemical Outcome 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
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References

  1. 1.
    Hurd CD, Bonner WA (1945) J Am Chem Soc 67:1972CrossRefGoogle Scholar
  2. 2.
    Hurd CD, Holysz RP (1950) J Am Chem Soc 72: 1732, 1735, 2005CrossRefGoogle Scholar
  3. 3.
    Helferich B, Bettin L (1961) Chem Ber 1158Google Scholar
  4. 4.
    Suhadolnik RJ (1970) Nucleoside antibiotics. Wiley-Interscience, New YorkGoogle Scholar
  5. 5.
    De Clercq E (1989) J Antimicrob Chemotherapy 23:35Google Scholar
  6. 6.
    Kobata A (1987) Malignant transformational changes of the sugar chain and their clinical applications. In: Greene MI, Hamaoca T (Eds) Development and recognition of the transformed cells. Plenum New York, p 385Google Scholar
  7. 7.
    Bernacki RI, Niedbala MJ, Korytnyk W (1985) Cancer Metastasis Rev 4:81CrossRefGoogle Scholar
  8. 8.
    Pili R, Chang J, Patris RA, Mueller RA, Chrest FJ, Passaniti A (1995) Cancer Res 55: 2920Google Scholar
  9. 9.
    Hers HG, (1984) Biochem Soc Trans 12:729Google Scholar
  10. 10.
    Hart GW (1992) Curr Op Cell Biol 4:1017CrossRefGoogle Scholar
  11. 11.
    Tschesche R, Widera W (1982) Liebigs Ann 902Google Scholar
  12. 12.
    Nicotra F, Ronchetti F, Russo G (1982) J Org Chem 47:4459CrossRefGoogle Scholar
  13. 13.
    Chem Abstr 65:790hGoogle Scholar
  14. 14.
    Lewis MD, Cha JK, Kishi Y (1982) J Am Chem Soc 104:4976CrossRefGoogle Scholar
  15. 15.
    Nicotra F, Panza L, Russo G (1987) J Org Chem 52:5627CrossRefGoogle Scholar
  16. 16.
    Nicotra F, Panza L, Russo G, Senaldi A, Burlini N, Tortora P (1990) J Chem Soc Chem Commun 1396Google Scholar
  17. 17.
    Dyer UC, Kishi Y (1988) J Org Chem 53: 3383; O’Leary DJ, Kishi Y (1993) J Org Chem 58:308CrossRefGoogle Scholar
  18. 18.
    Carcano M, Nicotra F, Panza L, Russo G (1989) J Chem Soc Chem Commun 642; Lay L, Nicotra F, Pangrazio C, Panza L, Russo G (1994) J Chem Soc Perkin Trans 1 333Google Scholar
  19. 19.
    Boschetti A, Nicotra F, Panza L, Russo G, Zucchelli L (1989) J Chem Soc Chem Commun 1085Google Scholar
  20. 20.
    Lay L, Nicotra F, Russo G, Caneva E (1992) J Org Chem 57:1304CrossRefGoogle Scholar
  21. 21.
    Cipolla L, Lay L, Nicotra F (1996) Carbohydr Lett 2: 131Google Scholar
  22. 22.
    Wilcox CS, Long GH, Suh H (1984) Tetrahedron Lett 25:395; RajanBabu TU, Reddy GS (1986) J Org Chem 51:5458CrossRefGoogle Scholar
  23. 23.
    Herpin TF, Motherwell WB, Tozer MJ (1994) Tetrahedron: Asymm 5:2269CrossRefGoogle Scholar
  24. 24.
    Chapleur Y (1984) J Chem Soc Chem Commun 449Google Scholar
  25. 25.
    Cipolla L,Liguori L, Nicotra F, Torri G, Vismara E (1996) J Chem Soc Chem Commun, 1253Google Scholar
  26. 26.
    Shirahashi H, Murakami N, Watanabe M, Nagatsu A, Sakakibara J, Tokuda H, Nishino H, Iwashima A (1993) Chem Pharm Bull 41: 1664Google Scholar
  27. 27.
    Ohrui H, Jones HJ, Moffatt JG, Maddox ML, Christensen AT, Bryan SK (1975) J Am Chem Soc 97:4602CrossRefGoogle Scholar
  28. 28.
    Hanessian S, Ogawa T, Guindon Y (1974) Carbohydr Res 34: C12CrossRefGoogle Scholar
  29. 29.
    Nicotra F, Ronchetti F, Russo G (1982) J Org Chem 47:5381CrossRefGoogle Scholar
  30. 30.
    Nicotra F, Russo G, Ronchetti F, Toma L (1983) Carbohydr Res 124:C5CrossRefGoogle Scholar
  31. 31.
    Fraser-Reid B, Dawe RD, Tulshian DH (1979) Can J Chem 57: 1746CrossRefGoogle Scholar
  32. 32.
    Pougny J-R, Nassr MAM, Sinay P (1881) J Chem Soc Chem Commun 375Google Scholar
  33. 33.
    Nicotra F, Perego R, Ronchetti F, Russo G, Toma L (1984) Gazz Chim Ital 114: 193Google Scholar
  34. 34.
    Reitz AB, Nortey SO, Maryanoff BE, Liotta D, Monahan R (1987) J Org Chem 52:4191CrossRefGoogle Scholar
  35. 35.
    Nicotra F, Panza L, Ronchetti F, Russo G, Toma L (1987) Carbohydr Res 171: 49CrossRefGoogle Scholar
  36. 36.
    Nicotra F, Perego R, Ronchetti F, Russo G, Toma L (1984) Carbohydr Res 131: 180CrossRefGoogle Scholar
  37. 37.
    Nicotra F, Panza L, Ronchetti F, Toma L (1984) Tetrahedron Lett 25: 5937CrossRefGoogle Scholar
  38. 38.
    Boschetti A, Nicotra F, Panza L, Russo G (1988) J Org Chem 53: 4181CrossRefGoogle Scholar
  39. 39.
    Carcano M, Nicotra F, Panza L, Russo G (1989) J Chem Soc Chem Commun 297Google Scholar
  40. 40.
    Lay L, Nicotra F, Panza L, Verani A (1992) Gazz Chim Ital 122:345Google Scholar
  41. 41.
    Casero F, Cipolla L, Nicotra F, Panza L, Russo G (1996) J Org Chem, 61:3428CrossRefGoogle Scholar
  42. 42.
    Lichtentaler FW, Kaji E (1985) Liebigs Ann Chem 1659 and references cited thereinGoogle Scholar
  43. 43.
    Wong C-H, Halcomb RL, Ichikawa Y, Kajimoto T (1995) Angew Chem Int Ed Engl 34:412CrossRefGoogle Scholar
  44. 44.
    Bennek JA, Gray GIR (1987) J Org Chem 52:892CrossRefGoogle Scholar
  45. 45.
    Nicotra F, Panza L, Russo G, Verani A (1993) Tetrahedron: Asymm 4: 1203CrossRefGoogle Scholar

Copyright information

© Springer Verlag Berlin Heidelberg 1997

Authors and Affiliations

  • Francesco Nicotra
    • 1
  1. 1.Dipartimento di Chimica Organica e IndustrialeUniversità degli Studi di MilanoMilanoItaly

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