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Synthesis of aza-analogues of the glycosylated tyrosine portion of mannopeptimycin-E.

ABSTRACT: Two C4' amido disaccharide analogues of mannopeptimycin-E were synthesized via an iterative palladium glycosylation sequence. The stereoselective synthesis of the C4' acylated 1,4-alpha,alpha-manno,manno-amido disaccharide has been achieved in ten steps from a protected d-tyrosine. The path relies upon a regio- and diastereoselective palladium-catalyzed azide substitution reaction. The competence of the synthesis is demonstrated by the good overall yield (21%) from protected tyrosine.

SUBMITTER: Guppi SR

PROVIDER: S-EPMC2546506 | biostudies-literature | 2007 Jun

REPOSITORIES: biostudies-literature

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Synthesis of aza-analogues of the glycosylated tyrosine portion of mannopeptimycin-E.

Guppi Sanjeeva R SR O'Doherty George A GA

The Journal of organic chemistry 20070526 13

Two C4' amido disaccharide analogues of mannopeptimycin-E were synthesized via an iterative palladium glycosylation sequence. The stereoselective synthesis of the C4' acylated 1,4-alpha,alpha-manno,manno-amido disaccharide has been achieved in ten steps from a protected d-tyrosine. The path relies upon a regio- and diastereoselective palladium-catalyzed azide substitution reaction. The competence of the synthesis is demonstrated by the good overall yield (21%) from protected tyrosine. ...[more]

PMID: 17530803

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