Accession Number : AD0769163

Title :   Preparation of glycosides of 2-deoxy-2-methylamino-D-mannose, 2-deoxy-2-methylamino-D-glucose, and 2-deoxy-2-methylamino-D-galactose: Observations on N-methylation of amides.

Corporate Author : NATIONAL RESEARCH COUNCIL OF CANADA SASKATOON (SASKATCHEWAN) PRAIRIE REGIONAL LAB

Personal Author(s) : Gorin,P. A. J.

Report Date : 06 NOV 1972

Pagination or Media Count : 16

Abstract : Benzyl 2-((benzyloxycarbonyl)methylamino)-2-deoxy-alpha-D-mannopyranoside and its furanose isomer, the derived N-methyloxazolidinones, benzyl 2-((benzyloxycarbonyl)methylamino)-2-deoxy-beta-D-glucofuranoside and methyl 2-deoxy-2-methylacetamido-beta-D-galactofuranoside, were prepared from appropriate diethyl dithioacetals. They were considered the most suitable starting materials for synthesis of O-methyl-2-deoxy-2-methylamino-hexoses because of their ease of preparation and the presence of suitable blocking groups. Oxazolidinones were prepared from N-benzyloxycarbonyl derivatives of 2-amino-2-deoxy-D-mannose by using methanolic sodium methoxide. Their use in preparation of 2-deoxy-2-methyl-amino derivatives is discussed. The Kuhn reagent was used in these syntheses for N-methylating amides. However, certain amides containing comparatively bulky substituents in the vicinity of the NH group are resistant to methylation. (Author)

Descriptors :   (*Glycosides, Synthesis(Chemistry)), (*Hexoses, Synthesis(Chemistry)), (*Amides, Chemical reactions), Acetals, Canada

Subject Categories : Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE