NUCLEOPHILIC-SUBSTITUTION VERSUS RADICAL REACTION FOR CARBOHYDRATES DEOXYGENATION - APPLICATION AT C-4 OF METHYL-ALPHA-D-GLUCOPYRANOSIDE DERIVATIVES

Authors
CZERNECKI S HORNS S VALERY JM
Citation
S. Czernecki et al., NUCLEOPHILIC-SUBSTITUTION VERSUS RADICAL REACTION FOR CARBOHYDRATES DEOXYGENATION - APPLICATION AT C-4 OF METHYL-ALPHA-D-GLUCOPYRANOSIDE DERIVATIVES, Journal of carbohydrate chemistry, 14(1), 1995, pp. 157-163
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology
Journal title
Journal of carbohydrate chemistry → ACNP
ISSN journal
07328303
Volume
14
Issue
1
Year of publication
1995
Pages
157 - 163
Database
ISI
SICI code
0732-8303(1995)14:1<157:NVRRFC>2.0.ZU;2-H
Abstract
Two methods for deoxygenation at C-4 of methyl 2,3-di-O-benzyl-alpha-D -glucopyranoside are reported. The first one involves nucleophilic dis placement of a secondary methane sulfonate by lithium triethylborohydr ide to afford methyl ,3-di-O-benzyl-4-deoxy-alpha-D-xylo-hexopyranosid e (5). Compound 5 was also obtained in similar yield (approximate to 6 0%) by radical deoxygenation with tri-n-butyltin hydride of a thiocarb onylated derivative.