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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.
NATIONAL RESEARCH COUNCIL OF CANADA SASKATOON (SASKATCHEWAN) PRAIRIE REGIONAL LAB
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Benzyl 2-benzyloxycarbonylmethylamino-2-deoxy-alpha-D-mannopyranoside and its furanose isomer, the derived N-methyloxazolidinones, benzyl 2-benzyloxycarbonylmethylamino-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
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