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AuCl₃-Catalyzed Hemiacetal Activation for the Stereoselective Synthesis of 2-Deoxy Trehalose Derivatives.

ABSTRACT: A new practical, catalytic, and highly stereoselective method for directly accessing 1,1-α,α'-linked 2-deoxy trehalose analogues via AuCl₃-catalyzed dehydrative glycosylation using hemiacetal glycosyl donors and acceptors is described. The method relies on the chemoselective Brønsted acid-type activation of tribenzylated 2-deoxy hemiacetals in the presence of other less reactive hemiacetals.

SUBMITTER: Jeanneret R

PROVIDER: S-EPMC9442795 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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AuCl3-Catalyzed Hemiacetal Activation for the Stereoselective Synthesis of 2-Deoxy Trehalose Derivatives.

Jeanneret Robin R Walz Carlo C van Meerbeek Maarten M Coppock Sarah S Galan M Carmen MC

Organic letters 20220822 34

A new practical, catalytic, and highly stereoselective method for directly accessing 1,1-α,α'-linked 2-deoxy trehalose analogues via AuCl3-catalyzed dehydrative glycosylation using hemiacetal glycosyl donors and acceptors is described. The method relies on the chemoselective Brønsted acid-type activation of tribenzylated 2-deoxy hemiacetals in the presence of other less reactive hemiacetals. ...[more]

PMID: 35994370

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