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Direct synthesis of diastereomerically pure glycosyl sulfonium salts.

ABSTRACT: It is reported that stable glycosyl sulfonium salts can be generated via direct anomeric S-methylation of ethylthioglycosides. Mechanistically, this pathway represents the first step in the activation of thioglycosides for glycosidation; however, it can further allow for the synthesis and isolation of quasi-stable sulfonium ions, representing a new approach for studying these key intermediates.

SUBMITTER: Mydock LK

PROVIDER: S-EPMC3104671 | biostudies-literature | 2011 Jun

REPOSITORIES: biostudies-literature

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Direct synthesis of diastereomerically pure glycosyl sulfonium salts.

Mydock Laurel K LK Kamat Medha N MN Demchenko Alexei V AV

Organic letters 20110512 11

It is reported that stable glycosyl sulfonium salts can be generated via direct anomeric S-methylation of ethylthioglycosides. Mechanistically, this pathway represents the first step in the activation of thioglycosides for glycosidation; however, it can further allow for the synthesis and isolation of quasi-stable sulfonium ions, representing a new approach for studying these key intermediates. ...[more]

PMID: 21563800

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