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

Ji Zhang | Zendy; Niek N. H. M. Eisink | Zendy; Martin D. Witte | Zendy; Adriaan J. Minnaard | Zendy

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

Author(s) -

Ji Zhang,

Niek N. H. M. Eisink,

Martin D. Witte,

Adriaan J. Minnaard

Publication year - 2018

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.8b01949

Subject(s) - chemistry , regioselectivity , glucosamine , selectivity , isopropyl , branching (polymer chemistry) , palladium , catalysis , carbon skeleton , organic chemistry , stereochemistry , combinatorial chemistry

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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