Literature DB >> 17048851

S-adenosylhomocysteine analogues with the carbon-5' and sulfur atoms replaced by a vinyl unit.

Daniela Andrei1, Stanislaw F Wnuk.   

Abstract

Cross-metathesis of suitably protected 5'-deoxy-5'-methyleneadenosines with racemic and chiral N-Boc-protected six-carbon amino acids bearing a terminal double bond in the presence of the Hoveyda-Grubbs catalyst gave adenosylhomocysteine analogues with the C5'-C6' double bond. Bromination with pyridinium tribromide and dehydrobromination with DBU followed by standard deprotections yielded the 5'-(bromo)vinyl analogue. [structure: see text]

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Year:  2006        PMID： 17048851      PMCID： PMC2532837          DOI： 10.1021/ol062026m

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


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