Stereospecific synthesis of α-C-glycosyl derivatives ('α-C- glycosides') of N-acetylneuraminic acid by samarium-mediated reductive desulfonylation of a glycosyl phenylsulfone

Carbohydrate Research

Volumn 308, Issue 1-2, 1998, Pages 161-164

  Du, Yuguo ^a   Linhardt, Robert J ^a  

^a UNIVERSITY OF IOWA   (United States)

Author keywords

Barbier reaction; C glycosides; C glycosyl compounds; Neu5Ac; Phenylsulfone; Samarium diiodide

Indexed keywords

1 C [(METHYL 5 ACETAMIDO 4,7,8,9 TETRA O ACETYL 3,5 DIDEOXY DEXTRO GLYCERO ALPHA DEXTRO GALACTO NON 2 ULOPYRANOSYL)ONATE]CYCLOPENTA 1 OL; 1 C [(METHYL 5 ACETAMIDO 4,7,8,9 TETRA O ACETYL 3,5 DIDEOXY DEXTRO GLYCERO ALPHA DEXTRO GALACTO NON 2 ULOPYRANOSYL)ONATE]OCTAN 1 OL; 6 C [(METHYL 5 ACETAMIDO 4,7,8,9 TETRA O ACETYL 3,5 DIDEOXY DEXTRO GLYCERO ALPHA DEXTRO GALACTO NON 2 ULOPYRANOSYL)ONATE] 1,2 3,4 DI O ISOPROPYLIDENE ALPHA DEXTRO GALACTOPYRANOSE; DISACCHARIDE; GLYCOSIDE; GLYCOSYL PHENYLSULFONE; METHYL 5 ACETAMIDO 4,7,8,9 TETRA O ACETYL 2,6 ANHYDRO 2,3,5 TRIDEOXY DEXTRO GLYCERO ALPHA DEXTRO GALACTO NONONATE; N ACETYLNEURAMINIC ACID DERIVATIVE; SAMARIUM; SIALIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; GLYCOSYLATION; PRIORITY JOURNAL; REDUCTION; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0032029423     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(98)00054-8     Document Type: Article

References (18)

1. A. Varki, Glycobiology, 2 (1992) 25-40.
2. A. Wei, A. Haudrechy, C. Audin, C.-H. Jun, N. Haudrechy-Bretel, and Y. Kishi, J. Org. Chem., 60 (1995) 2160-2169.
3. D.E. Levy and C. Tang, The Chemistry of C-glycosides; Pergamon Press, Exeter, UK, 1995.
4. I.R. Vlahov, P.I. Vlahova, and R.J. Linhardt, J. Am. Chem. Soc., 119 (1997) 1480-1481.
5. D. Mazéas, T. Skrydstrup, O. Doumeix, and J.-M. Beau, Angew. Chem. Int. Ed. Engl., 33 (1994) 1383-1386; T. Skrydstrup, D. Mazéas, M. Elmouchir, G. Doisneau, C. Riche, A. Chiaroni, and J.-M. Beau, Chem. Eur. J., 3 (1997) 1342-1356.
6. D. Mazéas, T. Skrydstrup, O. Doumeix, and J.-M. Beau, Angew. Chem. Int. Ed. Engl., 33 (1994) 1383-1386; T. Skrydstrup, D. Mazéas, M. Elmouchir, G. Doisneau, C. Riche, A. Chiaroni, and J.-M. Beau, Chem. Eur. J., 3 (1997) 1342-1356.
7. D. Mazéas, T. Skrydstrup, and J.-M. Beau, Angew. Chem. Int. Ed. Engl., 34 (1995) 909-912; O. Jarreton, T. Skrydstrup, and J.-M. Beau, J. Chem. Soc., Chem. Commun., (1996) 1661-1662; D. Urban, T. Skrydstrup, C. Riche, A. Chiaroni, and J.-M. Beau, J. Chem. Soc., Chem. Commun., (1996) 1883-1884.
8. D. Mazéas, T. Skrydstrup, and J.-M. Beau, Angew. Chem. Int. Ed. Engl., 34 (1995) 909-912; O. Jarreton, T. Skrydstrup, and J.-M. Beau, J. Chem. Soc., Chem. Commun., (1996) 1661-1662; D. Urban, T. Skrydstrup, C. Riche, A. Chiaroni, and J.-M. Beau, J. Chem. Soc., Chem. Commun., (1996) 1883-1884.
9. D. Mazéas, T. Skrydstrup, and J.-M. Beau, Angew. Chem. Int. Ed. Engl., 34 (1995) 909-912; O. Jarreton, T. Skrydstrup, and J.-M. Beau, J. Chem. Soc., Chem. Commun., (1996) 1661-1662; D. Urban, T. Skrydstrup, C. Riche, A. Chiaroni, and J.-M. Beau, J. Chem. Soc., Chem. Commun., (1996) 1883-1884.
10. P. de Pouilly, A. Chénedé, J.-M. Mallat, and P. Sinaÿ, Bull. Soc. Chim. Fr., 130 (1993) 256-265.
11. S.-C. Hung and C.-H. Wong, Angew. Chem. Int. Ed. Engl., 35 (1996) 2671-2674.
12. G.A. Molander and C.R. Harris, Chem. Rev., 96 (1996) 307-338.
13. A. Marra and P. Sinaÿ, Carbohydr. Res., 187 (1989) 35-42.
14. O. Kanie, M. Kiso, and A. Hasegawa, J. Carbohydr. Chem., 7 (1988) 501-506.
15. R. R. Schmidt and A. Beyerbach, Liebigs Ann. Chem., 1992, 983-986.
16. B.P. Bandgar, M. Hartmann, W. Schmid, and E. Zbiral, Liebig Ann. Chem., (1990), 1185-1195.
17. D. B. Dess and J. C. Martin, J. Am. Chem. Soc., 113 (1991) 7277-7287.
18. W. Schmid, R. Christian, and E. Zbiral, Tetrahedron Lett., 29 (1988) 3643-3646.