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Synthetic studies toward mannopeptimycin-E: synthesis of the O-linked tyrosine 1,4-alpha,alpha-manno,manno-pyranosyl pyranoside.

ABSTRACT: [structure: see text] The enantioselective synthesis of the C-4' acylated 1,4-alpha,alpha-manno,manno-disaccharide fragment of mannopeptimycin-E has been achieved in seven steps from d-tyrosine. The route relies upon diastereoselective palladium-catalyzed glycosylation, diastereoselective reduction, and diastereoselective bis-dihydroxylation. The efficiency of the synthesis is demonstrated by the high overall yield (37%) and the preparation of various analogues.

SUBMITTER: Babu RS

PROVIDER: S-EPMC2631387 | biostudies-literature | 2006 Apr

REPOSITORIES: biostudies-literature

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Synthetic studies toward mannopeptimycin-E: synthesis of the O-linked tyrosine 1,4-alpha,alpha-manno,manno-pyranosyl pyranoside.

Babu Ravula Satheesh RS Guppi Sanjeeva R SR O'Doherty George A GA

Organic letters 20060401 8

[structure: see text] The enantioselective synthesis of the C-4' acylated 1,4-alpha,alpha-manno,manno-disaccharide fragment of mannopeptimycin-E has been achieved in seven steps from d-tyrosine. The route relies upon diastereoselective palladium-catalyzed glycosylation, diastereoselective reduction, and diastereoselective bis-dihydroxylation. The efficiency of the synthesis is demonstrated by the high overall yield (37%) and the preparation of various analogues. ...[more]

PMID: 16597121

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