Regioselective Manipulation of GlcNAc Provides Allosamine, Lividosamine, and Related Compounds.
Ji ZhangNiek N H M EisinkMartin D WitteAdriaan J MinnaardPublished in: The Journal of organic chemistry (2019)
Palladium-catalyzed oxidation of isopropyl N-acetyl-α-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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