Table of Contents
Research Letters in Organic Chemistry
Volume 2008, Article ID 784173, 4 pages
http://dx.doi.org/10.1155/2008/784173
Research Letter

Syntheses of 5-Thio-D-Mannose from Petrochemicals and a Disaccharide Analog Containing It

Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan

Received 8 April 2008; Accepted 11 May 2008

Academic Editor: Robin Polt

Copyright © 2008 Hideya Yuasa et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

Per- 𝑂 -acetyl-5-thio-DL-mannose was synthesized from petrochemicals in six steps and 9% overall yield. It was then derivatized into glycosyl trichloroacetimidate and subjected to glycosidation reaction with a mannosyl acceptor to give a separatable mixture of disaccharides with 5-thio-D- and L-mannosides. This is the first synthesis of an enantiomerically pure 5-thiosugar derivative from racemic chemicals. The D-glycoside was derivatized into methyl (5-thio- 𝛼 -D-mannopyranosyl)-2- 𝑂 - 𝛼 -D-mannopyranoside 6-phosphate as a potential inhibitor of a golgi 𝛼 -1,2-mannosidase.