Synthesis of 2-acetamido-2-deoxy-D-gulose, 2-acetamido-2-deoxy-D-idose, and 2-deoxy-D-xylo-hexose from 3,4,5,6-tetraacetoxy-D-xylo-1-nitro-1-hexene

Author:

Perry M. B.,Webb Ann C.

Abstract

3,4,5,6-Tetraacetoxy-D-xylo-1-nitro-1-hexene with methanolic ammonia afforded a mixture of 2-acetamido-1,2-dideoxy-1-nitro-D-gulitol and 2-acetamido-1,2-dideoxy-1-nitro-D-iditol which were converted via a Nef reaction to 2-acetamido-2-deoxy-D-gulose and 2-acetamido-2-deoxy-D-idose.Reduction of 3,4,5,6-tetraacetoxy-D-xylo-1-nitro-1-hexene afforded 3,4,5,6-tetra-O-acetyl-1,2-dideoxy-1-nitro-D-xylo-hexitol which was converted via the Nef reaction to 2-deoxy-D-xylo-hexose.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

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1. Selective Axial-to-Equatorial Epimerization of Carbohydrates;Journal of the American Chemical Society;2022-06-22

2. Synthesis of 6-Deoxyamino Sugars;Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products;1998

3. The Nef Reaction;Organic Reactions;1990-04-05

4. Syntheses of 2,3,6-trideoxy-3-amino- and 2,3,6-trideoxy-3-nitrohexoses;Chemical Reviews;1986-02

5. Separation of eight epimeric 2-aminoaldohexoses as aminohexitol acetates by gas chromatography and analysis of bacterial heteroglycans containing rare 2-aminoaldohexoses and 2-aminouronic acids;Journal of Chromatography A;1984-01

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