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Benzyne arylation of oxathiane glycosyl donors.

ABSTRACT: The arylation of bicyclic oxathiane glycosyl donors has been achieved using benzyne generated in situ from 1-aminobenzotriazole (1-ABT) and lead tetraacetate. Following sulfur arylation, glycosylation of acetate ions proceeded with high levels of stereoselectivity to afford α -glycosyl acetates in a 'one-pot' reaction, even in the presence of alternative acceptor alcohols.

SUBMITTER: Fascione MA

PROVIDER: S-EPMC2870982 | biostudies-literature | 2010 Feb

REPOSITORIES: biostudies-literature

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Benzyne arylation of oxathiane glycosyl donors.

Fascione Martin A MA Turnbull W Bruce WB

Beilstein journal of organic chemistry 20100222

The arylation of bicyclic oxathiane glycosyl donors has been achieved using benzyne generated in situ from 1-aminobenzotriazole (1-ABT) and lead tetraacetate. Following sulfur arylation, glycosylation of acetate ions proceeded with high levels of stereoselectivity to afford α -glycosyl acetates in a 'one-pot' reaction, even in the presence of alternative acceptor alcohols. ...[more]

PMID: 20485601

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