Efficient stereoselective synthesis of 1-thio-beta-mannopyranosides

Authors
Yu, HN Ling, CC Bundle, DR
Citation
Hn. Yu et al., Efficient stereoselective synthesis of 1-thio-beta-mannopyranosides, J CHEM S P1, (8), 2001, pp. 832-837
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14727781 → ACNP
Issue
8
Year of publication
2001
Pages
832 - 837
Database
ISI
SICI code
1472-7781(2001):8<832:ESSO1>2.0.ZU;2-6
Abstract
An efficient method for the synthesis of 1-thio-beta -mannopyranosides is r eported. This method employs the simple, easy-to-make 2,3,4,6-tetra-O-acety l-1-S-acetyl-1-thio-beta -D-mannopyranose as starting material to conduct a n in situ selective de-S-acetylation, and subsequent S(N)2 reaction with an acceptor bearing a leaving group. The high nucleophilicity and slow anomer ization of the intermediate thiol allows the synthesis of 1-thio-beta -mann opyranosides in a simple and practical manner.