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For deoxy analogues of N-acetyl-D-glucosamine and three deoxy-analogues of phenyl N-acetyl-β-D-glucosaminide were synthesized by means of chlorination with sulfuryl chloride and reduction of the chlorides with tri-n-butyltin hydride. The free sugars thus obtained failed to crystallize except for 6-deoxy and 4,6-dideoxy compounds. Phenyl glycosides were mostly crystalline. The yield of chlorination and reduction was generally high.

Benzyl 2-acetamido-6-O-acetyl-4-chloro-2,4-dideoxy-3-O-[D-1-(methyl carboxylate)ethyl]-α-D-galactopyrano-side and benzyl 2-acetamido-4,6-dichloro-2,4,6-trideoxy-3-O-[D-1-(methyl carboxylate) ethyl]-α-D-galactopyranoside were prepared by the reaction of sulfuryl chloride on N-acetyl-muramic acid derivatives. 2-Acetamido-2,4-dideoxy-3-O-(D-1-carboxyethyl)-D-xylohexo-pyranose (N-acetyl-4-deoxy-muramic acid) and 2-acetamido-2,4,6-trideoxy-3-O-(D-1-carboxyethyl)-D-xylohexo-pyranose (N-acetyl-4,6-dideoxy-muramic acid) were prepared by the reduction of these chlorodeoxy derivatives with tri-n-butyltin hydride.