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A concise C-glycosyl amino acids synthesis by alkenyl C-glycoside-vinyloxazolidine cross-metathesis. Synthesis of glycosyl serine, asparagine and hydroxynorvaline isosteres

By DONDONI A, GIOVANNINI PP and MARRA A.

Abstract

: A convergent synthesis has been developed to afford C-linked glycosyl amino acids by cross metathesis of vinyl, allyl, and butenyl C-glycosides with N-Boc vinyloxazolidine using the Grubbs 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ruthenium carbene. The method has been employed to introducing through an alpha-linkage an alpha-amino pentanoic acid chain at the anomeric carbon of beta-D-C-gentiobiose to give a totally artificial glycosyl alpha-amino acid of a disaccharide. This compound represents the isostere of the alpha-linked glycosyl asparagine moiety of the natural glycopeptide nephritogenosid

Year: 2001
OAI identifier: oai:iris.unife.it:11392/1205658
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