First synthesis of anomeric sulfimides - Efficient glycosyl donors

Tetrahedron Letters

Volumn 39, Issue 44, 1998, Pages 8097-8100

  Cassel, Stéphanie ^a   Plessis, Isabelle ^b   Wessel, Hans Peter ^b   Rollin, Patrick ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2 PROPANOL; CARBOHYDRATE DERIVATIVE; GLUCOSE; METHANOL; SULFIMIDE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; GLYCOSYLATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032578815     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01837-1     Document Type: Article

References (18)

1. 1. G. Smith, T. J. Sparey and P. C. Taylor, J. Chem. Soc. Perkin Trans I (1996) 313-317 and references cited.
2. 2. selected references for a) sulfoxides : S. Cassel, P. Chaimbault, M. Lafosse; C. Lorin and P. Rollin, Sulfur Lett., 20 (1996) 63-70
3. b) vinyl sulfides : L. Brochard, C. Lorin, N. Spiess and P. Rollin, Tetrahedron Lett., 39 (1998) 4267-4270.
4. 3. see related study in : H. Yuasa, T. Kajimoto and C.-H. Wong, Tetrahedron Lett., 35 (1994) 8243-8246.
5. 4. C. R. Johnson, K. Mori and A. Nakanishi, J. Org. Chem., 44 (1979) 2065-2067.
6. 4, filtered and the filtrate evaporated under reduced pressure.
7. 1H-NMR and mass spectrometry) were obtained for compounds 2a-f.
8. 7. K. Toshima and K. Tatsuta, Chem. Rev., 93 (1993) 1503-1531.
9. 8. P. J. Garegg, Adv. Carbohydr. Chem. Biochem., 52 (1997) 179-205.
10. 9. J.-R. Pougny, J. Carbohydr. Chem., 5 (1986) 529-535.
11. 10. A. Marra, F. Gauffeny and P. Sinaÿ, Tetrahedron, 47 (1991) 5149-5160.
12. 11. P. Fügedi, P.J. Garegg, S. Oscarson, G. Rosén and B.A. Silwanis, Carbohydr. Res., 211 (1991) 157-162.
13. 12. L. Yan and D. Kahne, J. Am. Chem. Soc., 118 (1996) 9239-9248 and references cited.
14. 13. D. Crich and S. Sun, J. Am. Chem. Soc., 120 (1998) 435-436.
15. 14. T. Mukaiyama, T. Nakatsuka and S.-I. Shoda, Chem. Lett. (1979) 487-490; see also A. Dondoni, A. Marra, M.-C. Scherrmann, A. Casnati, F. Sansone and R. Ungaro, Chem. Eur. J., 3 (1997) 1774-1782.
16. 14. T. Mukaiyama, T. Nakatsuka and S.-I. Shoda, Chem. Lett. (1979) 487-490; see also A. Dondoni, A. Marra, M.-C. Scherrmann, A. Casnati, F. Sansone and R. Ungaro, Chem. Eur. J., 3 (1997) 1774-1782.
17. 15. NB : the sulfimides 2 involved in the glycosylation reactions were used without purification.
18. 2 (3.3 equivalents). After 5 min stirring (in the case of the per-benzylated donor), two drops of triethylamine were added and the mixture was stirred for another 5 min, filtered over Celite®, and the filtrate was evaporated under reduced pressure. The disaccharides 3 were purified by silica gel column chromatography.