syntheses of 5-thio-d-mannose from petrochemicals and a disaccharide analog containing it合成的5-thio-d-mannose石化和二糖模拟包含它.pdfVIP

Hindawi Publishing Corporation Research Letters in Organic Chemistry Volume 2008, Article ID 784173, 4 pages doi:10.1155/2008/784173 Research Letter Syntheses of 5-Thio-D-Mannose from Petrochemicals and a Disaccharide Analog Containing It Hideya Yuasa, Masatake Jouyabu, Nobuyuki Mitsuhashi, and Hironobu Hashimoto Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan Correspondence should be addressed to Hideya Yuasa, hyuasa@bio.titech.ac.jp Received 8 April 2008; Accepted 11 May 2008 Recommended by Robin Polt 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. 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. 1. Introduction derivative of 5SMan, which gave a diastereomeric mixture of 5SMan-containing disaccharides, and they were easily 5-thiosugars are aldopyranose analogs with a sulfur atom separated by column chromatography.