4.7 Article

Regioselective Manipulation of GlcNAc Provides Allosamine, Lividosamine, and Related Compounds

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 2, Pages 516-525

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01949

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Funding

  1. China Scholarship Council
  2. Dutch Science Foundation NWO [022.004.027]

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Palladium-catalyzed oxidation of isopropyl N-acetyl-alpha-D-glucosamine (GlcNAc) is used to prepare the rare sugars allosamine, lividosamine, and related compounds with unprecedented selectivity. The Passerini reaction applied on 3-keto-GlcNAc provides an entry into branching of the carbon skeleton in this compound.

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