SYNTHESIS OF A THIO-LINKED ANALOG OF SIALYL-LEWIS-X

Authors
EISELE T TOEPFER A KRETZSCHMAR G SCHMIDT RR
Citation
T. Eisele et al., SYNTHESIS OF A THIO-LINKED ANALOG OF SIALYL-LEWIS-X, Tetrahedron letters, 37(9), 1996, pp. 1389-1392
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
9
Year of publication
1996
Pages
1389 - 1392
Database
ISI
SICI code
0040-4039(1996)37:9<1389:SOATAO>2.0.ZU;2-A
Abstract
Thiolinked sialyl Lewis X analogue 2 was obtained from neuraminic acid , D-galactose, and L-fucose. Galactose was transformed into 3-thiogala ctose building block 6 and also into the required 3,4-dithioglucose mo iety. Thioglycoside bond formation was performed via base-promoted S-g lycosylation [Neu5Aca alpha(2-3S)Gal and Gal beta(1-4S)Glc linkages] a nd via acid catalyzed S-glycosylation [Fuca(1-3S)Glc and Glc beta-(1-1 S)heptyl linkages].