Synthesis and Stereochemistry of Some new Derivatives of 1,2-O-Cyclohexylidene-α-D-Xylofuranuronic Acid

Abstract

1,2-0-Cyclohexylidene-a-D-xylofuranuronic acid (2) has been converted into its 3-Q-acetyl derivative and consecutively to the corresponding acid chloride and ethyl ester. Direct reaction of 2 with ethanol in the presence of p-to-luene sulphonic acid gave the ethyl ester. Reaction of 2 with phosphorus pentachloride in dry ether gave the acid chloride of 1,2-0-cyclohexylidene-3-0-dichlorophosphoryl--a-D-xylofuranuronic acid. Conformational data have been obtained from 1H and 13C NMR measurements. © 1987, Taylor & Francis Group, LLC. All rights reserved.