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Cationic gold(I)-catalyzed glycosylation with glycosyl N-1,1-dimethylpropargyl carbamate donors.

ABSTRACT: A mild and efficient cationic gold(I)-catalyzed O-glycosylation methodology involving the use of bench-stable glycosyl N-1,1-dimethylpropargyl carbamate donors has been developed. In the presence of 1-2 mol% [tris(2,4-di-tert-butylphenyl)phosphite]gold(I) chloride and 5 mol% silver triflate, both "armed" and "disarmed" glycosyl N-1,1-dimethylpropargyl carbamate donors react with various sugar acceptors at room temperature to afford the corresponding glycosides in good to excellent yields. These glycosyl N-1,1-dimethylpropargyl carbamates are found to be orthogonal to regular phenyl thioglycoside donors. The utilization of this method has been demonstrated in the synthesis of a trisaccharide.

SUBMITTER: Gurung PB

PROVIDER: S-EPMC9540757 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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Cationic gold(I)-catalyzed glycosylation with glycosyl N-1,1-dimethylpropargyl carbamate donors.

Gurung Prem Bahadur PB Thapa Prakash P Hettiarachchi Ishani Lakshika IL Zhu Jianglong J

Organic & biomolecular chemistry 20220914 35

A mild and efficient cationic gold(I)-catalyzed O-glycosylation methodology involving the use of bench-stable glycosyl N-1,1-dimethylpropargyl carbamate donors has been developed. In the presence of 1-2 mol% [tris(2,4-di-tert-butylphenyl)phosphite]gold(I) chloride and 5 mol% silver triflate, both "armed" and "disarmed" glycosyl N-1,1-dimethylpropargyl carbamate donors react with various sugar acceptors at room temperature to afford the corresponding glycosides in good ...[more]

PMID: 36000552

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