Syntheses of 4-acetamido-4,5-dideoxy-D-xylofuranose and 5-acetamido-5,6-dideoxy-L-talofuranose

Abstract

4-Acetamido-4,5-dideoxy-D-xylose and 5-acetamido-5,6-dideoxy-L-talose have been synthesised from L-rhamnose. The former sugar is shown to exist predominantly as the pyrrolidine-type ring structure and, with the latter sugar, cyclisation on to the C(4) oxygen, to give the furanoid ring, is preferred to formation of the six-membered piperidine-type ring.