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De novo asymmetric synthesis of homoadenosine via a palladium-catalyzed N-glycosylation.

ABSTRACT: [reaction: see text] A highly stereoselective synthesis of l-2-deoxy-beta-ribo-hexopyranosyl nucleosides from 6-chloropurine and Boc-protected pyranone has been developed. Our approach relies on the iterative application of a palladium-catalyzed N-glycosylation, diastereoselective reduction, and reductive 1,3-transposition. This strategy is amenable to prepare various natural and unnatural hexopyranosyl nucleosides analogues.

SUBMITTER: Guppi SR

PROVIDER: S-EPMC2546502 | biostudies-literature | 2006 Jan

REPOSITORIES: biostudies-literature

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De novo asymmetric synthesis of homoadenosine via a palladium-catalyzed N-glycosylation.

Guppi Sanjeeva R SR Zhou Maoquan M O'Doherty George A GA

Organic letters 20060101 2

[reaction: see text] A highly stereoselective synthesis of l-2-deoxy-beta-ribo-hexopyranosyl nucleosides from 6-chloropurine and Boc-protected pyranone has been developed. Our approach relies on the iterative application of a palladium-catalyzed N-glycosylation, diastereoselective reduction, and reductive 1,3-transposition. This strategy is amenable to prepare various natural and unnatural hexopyranosyl nucleosides analogues. ...[more]

PMID: 16408898

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