Facile Preparation of Peracetates and Per-3-bromobenzoates of α-Mono- and Disaccharides.docVIP

Molecules 2005, 10, 1325-1334 molecules ISSN 1420-3049 Facile Preparation of Peracetates and Per-3-bromobenzoates of α-Mono- and Disaccharides Zerong (Daniel) Wang,* Mahfuza Matin and Samia Sheikh Department of Chemistry, School of Sciences and Computer Engineering, University of Houston- Clear Lake, 2700 Bay Area Boulevard, Houston, TX 77058, USA Tel. +1 (281)-283-3795, Fax +1 (281)-283-3709 * Author to whom correspondence should be addressed; e-mail: wang@ Received: 1 July 2005; in revised form: 12 July 2005 / Accepted: 12 July 2005 / Published: 31 October 2005 Abstract: A simple and convenient method for the preparation of fully acetylated and (3- bromo)benzoylated α-monosaccharides and disaccharides through vigorous mechanical mixing of solid reactants on a high speed shaker is described. Using this technique a variety of α-acylated sugars are prepared, including penta-O-acetyl-α-D-galactopyranose, penta-O- acetyl-α-D-glucopyranose, penta-O-acetyl-α-D-mannopyranose, octa-O-acetyl-α-lactose, penta-O-(3-bromo)benzoyl-α-D-galactopyranose, penta-O-(3-bromo)benzoyl-α-D-gluco- pyranose, penta-O-(3-bromo)benzoyl-α-D-mannopyranose, and octa-O-(3-bromo)benzoyl- α-lactose. Keywords: α-Galactose, α-glucose, α-mannose, lactose, mechanochemical mixing Introduction Mechanochemical methods have recently attracted much attention because of their inherent advantages, including less secondary reactions [1], high conversion yield within short reaction time [2], reduced pollution, low costs, and simplicity in processing and handling [3]. So far, mechanochemical methods have been successfully applied to areas such as decomposition of organic polymer wastes [1], degradation of organic compounds [4], single-crystal polymer synthesis [5], reduction of metal oxides in solid state [6], etc. More importantly, mechanochemical treatments have made many classic organic reactions which have traditionally