INTRAMOLECULAR GLYCOSIDATION - STEREOCONTROLLED SYNTHESIS OF ALPHA-GLUCOSIDES FROM A 2-O-ALKOXYSILYL THIOGLUCOSIDE

Authors
BOLS M
Citation
M. Bols, INTRAMOLECULAR GLYCOSIDATION - STEREOCONTROLLED SYNTHESIS OF ALPHA-GLUCOSIDES FROM A 2-O-ALKOXYSILYL THIOGLUCOSIDE, Acta chemica Scandinavica, 47(8), 1993, pp. 829-834
Citations number
27
Categorie Soggetti
Chemistry,Biology
Journal title
Acta chemica Scandinavica → ACNP
ISSN journal
0904213X
Volume
47
Issue
8
Year of publication
1993
Pages
829 - 834
Database
ISI
SICI code
0904-213X(1993)47:8<829:IG-SSO>2.0.ZU;2-2
Abstract
2-O-(Alkoxydimethyl)silylglucosyl piperidide, chloride and thiophenola te derivatives have been prepared, and intramolecular glycosidation of these derivatives was attempted. Reaction of phenyl 3,4,6-tri-O-acety l-2-O-(octyloxy-, cyclohexyloxy-, tert-butoxy- and noxy-dimethyl)Silyl -alpha-D-gluco-1-thiopyranoside with N-iodo-succinimide and trifluorom ethanesulfonic acid gave stereospecifically the corresponding alkyl 3. 4,6-tri-O-acetyl-alpha-D-glucopyranosides.