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. 2019 Jan 18;84(2):516-525.
doi: 10.1021/acs.joc.8b01949. Epub 2019 Jan 2.

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

Ji Zhang  1 , Niek N H M Eisink  1 , Martin D Witte  1 , Adriaan J Minnaard  1
Affiliations

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

Ji Zhang et al. J Org Chem. .

Abstract

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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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Site-Selective Palladium-Catalyzed Oxidation of Unprotected Carbohydrates
Scheme 2
Scheme 2. Jeanloz Synthesis of d-Allosamine and d-N-Acetyl Allosamine
Scheme 3
Scheme 3. Synthesis of d-Allosamine and N-Acetyl-d-allosamine
Figure 1
Figure 1
X-ray structure of boc-hydrazone 24.
Scheme 4
Scheme 4. Synthesis of d-Lividosamine
Scheme 5
Scheme 5. Synthesis of 2,3-Di-amino Glucose and a Corresponding Fused Imidazole
Scheme 6
Scheme 6. Passerini Reaction with 1-Isopropyl-3-keto GlcNAc
See this image and copyright information in PMC

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