Streamlined synthesis of per-O-acetylated sugars, glycosyl iodides, or thioglycosides from unprotected reducing sugars

Journal of Organic Chemistry

Volumn 69, Issue 22, 2004, Pages 7758-7760

  Mukhopadhyay, Balaram ^a   Kartha, K P Ravindranathan ^b   Russell, David A ^a   Field, Robert A ^a  

^a UNIVERSITY OF EAST ANGLIA   (United Kingdom)

^b NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLATION; CATALYSIS; IODINE COMPOUNDS; MIXTURES; SILANES; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ANOMERIC MIXTURES; ANOMERIC SUBSTITUTION; GLYCOSYL IODIDES; THIOGLYCOSIDES;

SUGARS;

ACETIC ANHYDRIDE; CARBOHYDRATE; DIMETHYL DISULFIDE; DISULFIDE; ETHANE; ETHANETHIOL; GLYCOSYL IODIDE DERIVATIVE; HEXAMETHYLDISILANE; IODINE; IODINE DERIVATIVE; PYRAN DERIVATIVE; REDUCING AGENT; SILANE DERIVATIVE; SOLVENT; THIOCRESOL; THIOGLYCOSIDE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REPRODUCIBILITY; STEREOCHEMISTRY; STOICHIOMETRY; SUBSTITUTION REACTION; SYNTHESIS; TECHNIQUE;

ACETYLATION; CARBOHYDRATES; CATALYSIS; GLYCOSIDES; IODINE; MOLECULAR STRUCTURE; THIOGLYCOSIDES;

EID: 6344293965     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048890e     Document Type: Article

References (43)

1. Iodine: a versatile reagent in carbohydrate chemistry XVI. For part XV, see: Marsh, S. J.; Kartha, K. P. R.; Field, R. A. Synlett 2003, 1376.
2. (a) Varki, A. Glycobiology 1993, 3, 97.
3. (b) Essentials of Glycobiology; Varki, A., Cummings, R., Esko, J., Freeze, H., Hart, G., Marth, J., Eds.; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY, 1999.
4. (c) Sears, P.; Wong, C.-H. Science 2001, 291, 2344.
5. Baeschlin, D. K.; Green, L. G.; Hahn, M. G.; Hinzen, B.; Ince, S. J.; Ley, S. V. Tetrahedron: Asymmetry 2000, 11, 173.
6. (a) Fraser-Reid, B.; Udodong, U. E.; Wu, Z. F.; Ottosson, H.; Merritt, J. R.; Rao, C. S.; Roberts, C.; Madsen, R. Synlett 1992, 927.
7. (b) Veeneman, G. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 275.
8. (a) Ye, X. S.; Wong, C.-H. J. Org. Chem. 2000, 65, 2410.
9. (b) Reviewed in: Sears, P.; Wong, C.-H. Science 2001, 291, 2344.
10. (a) Plante, O. J.; Palmacci, E. R.; Seeberger, P. H. Science 2001, 291, 1523.
11. (b) Seeberger, P. H., Ed. Solid Support Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries; Wiley-Interscience: New York, 2001.
12. For recent examples of the use of per-O-acetylated sugars as donors in O-glycoside synthesis, see: (a) Junot, N.; Meslin, J. C.; Rabiller, C. Tetrahedron: Asymmetry 1995, 6, 1387.
13. (b) Binch, H.; Stangier, K.; Thiem, J. Carbohydr. Res. 1998, 306, 409.
14. (c) Bhaskar, P. M.; Loganathan, D. Synlett 1999, 129.
15. (d) Kumareswaran, R.; Pachamuthu, K.; Vankar, Y. D. Synlett 2000, 11, 1652.
16. (e) Lee, J.-C.; Tai, C.-A.; Hung, S.-C. Tetrahedron Lett. 2002, 43, 851.
17. (f) Tai, C.-A.; Kulkarni, S. S.; Hung, S.-C. J. Org. Chem. 2003, 68, 8719.
18. (g) Davis, B. J.; Chambers, D.; Cumpstey, I.; France, R.; Gamblin, D. In Best Synthetic Methods: Carbohydrates; Osborn, H. M. I., Ed.; Academic Press: 2003; pp 69-120.
19. For recent examples of the use of glycosyl iodides in O-, C-, N-, and S-glycoside synthesis, see: (a) Gervay, J.; Hadd, M. J. J. Org. Chem. 1997, 62, 6961.
20. (b) Gervay, J. Organic Synthesis: Theory and Applications; JAI Press, Inc.: New York, 1998: Vol. 4, p 121.
21. (c) Hadd, M. J.; Gervay, J. Carbohydr. Res. 1999, 320, 61.
22. (d) Bhat, A. S.; Gervay-Hague, J. Org. Lett. 2001, 3, 2081.
23. (e) Lam, S. N.; Gervay-Hague, J. Carbohydr. Res. 2002, 337, 1953.
24. (f) Lam, S. N.; Gervay-Hague, J. Org. Lett. 2002, 4, 2039.
25. (g) Dabideen, D. R.; Gervay-Hague, J. Org. Lett. 2004, 6, 973.
26. (h) Miquel, N.; Vignando, S.; Russo, G.; Lay, L. Synlett 2004, 2, 341.
27. For recent examples of the use of thioglycosides in O-glycoside syntheses, see: (a) Garegg, P. J. Adv. Carbohydr. Chem. Biochem. 1997, 52, 1179.
28. (b) Das, S. K.; Roy, J.; Reddy, K. A.; Abbineni, C. Carbohydr. Res. 2003, 338, 2237.
29. (c) Yu, H.; Ensley, H. E. Tetrahedron Lett. 2003, 44, 9363.
30. (d) Mukhopadhyay, B.; Roy, N. Carbohydr. Res. 2003, 338, 589.
31. (e) Alpe, M.; Oscarson, S.; Svahnberg, P. J. Carbohydr. Chem. 2003, 22, 565.
32. (f) Kartha, K. P. R.; Field, R. A. In Best Synthetic Methods: Carbohydrates; Osborn, H. M. I., Ed.; Academic Press: Oxford, UK, 2003; pp 121-145.
33. (g) Mukhopadhyay, B.; Field, R. A. Carbohydr. Res. 2004, 339, 1285.
34. (h) Codée, J. D. C.; van den Bos, L. J.; Litjens, R. E. J. N.; Overkleeft, H. S.; van Boeckel, C. A. A.; van Boom, J. H.; van der Marel, G. A. Tetrahedron 2004, 60, 1057.
35. Kartha, K. P. R.; Field, R. A. Tetrahedron 1997, 53, 11753.
36. Kartha, K. P. R.; Field, R. A. Carbohydr. Lett. 1998, 3, 179.
37. Kartha, K. P. R.; Field, R. A. J. Carbohydr. Chem. 1998, 17, 693.
38. (a) Olah, G. A.; Narang, S. C.; Gupta, B. G. B.; Malhotra, R. Angew. Chem., Int. Ed. Engl. 1979, 18, 612.
39. (b) Olah, G. A.; Narang, S. C. Tetrahedron 1982, 38, 2225.
40. Phukan, P. Tetrahedron Lett. 2004, 45, 4785.
41. General concern about glycosyl iodide stability is unfounded. Crystalline glycosyl iodides were first reported almost a century ago: (a) Fisher, E.; Fischer, H. Ber. 1910, 43, 2535.
42. (b) Brauns, D. H. J. Chem. Soc. 1927, 49, 3170. In addition, the crystal structure of methyl 2,3,4-tri-O-pivaloyl-α-D-glucopyranosyluronate iodide has recently been reported: Bickley, J.; Cottrell, J. A.; Ferguson, J. R.; Field, R. A.; Harding, J. R.; Hughes, D. L.; Kartha, K. P. R.; Law, J. L.; Scheinmann, F.; Stachulski, A. V. Chem. Commun. 2003, 1266.
43. (b) Brauns, D. H. J. Chem. Soc. 1927, 49, 3170. In addition, the crystal structure of methyl 2,3,4-tri-O-pivaloyl-α-D-glucopyranosyluronate iodide has recently been reported: Bickley, J.; Cottrell, J. A.; Ferguson, J. R.; Field, R. A.; Harding, J. R.; Hughes, D. L.; Kartha, K. P. R.; Law, J. L.; Scheinmann, F.; Stachulski, A. V. Chem. Commun. 2003, 1266.