ACTION OF BASE ON METHYL DEOXY-)2-O-METHANESULFONYL-ALPHA-D-GLUCOPYRANOSIDE DERIVATIVES

Authors
IZQUIERDO I RODRIGUEZ M PLAZA MT PLEGUEZUELOS J
Citation
I. Izquierdo et al., ACTION OF BASE ON METHYL DEOXY-)2-O-METHANESULFONYL-ALPHA-D-GLUCOPYRANOSIDE DERIVATIVES, Journal of carbohydrate chemistry, 17(1), 1998, pp. 61-74
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology
Journal title
Journal of carbohydrate chemistry → ACNP
ISSN journal
07328303
Volume
17
Issue
1
Year of publication
1998
Pages
61 - 74
Database
ISI
SICI code
0732-8303(1998)17:1<61:AOBOMD>2.0.ZU;2-Z
Abstract
Treatment of methyl 2-O-methanesulfonyl-6-thio-alpha-D-glucopyranoside (8) and its 6-deoxy analogue (11) with methanolic sodium methoxide, a fforded methyl 2,3-anhydro-mannopyranoside derivatives as a consequenc e of an O-3 --> O-4 TBDPS rearrangement. When the protecting group at C-3 was 2-methoxyethoxy methyl ether only deacylation and methanolysis of the methanesulfonyl group occurred.