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

2001; Royal Society of Chemistry; Issue: 19 Linguagem: Inglês

10.1039/b106029p

1472-7781

Alessandro Dondoni, Pier Paolo Giovannini, Alberto Marra,

Glycosylation and Glycoproteins Research

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-ylideneruthenium carbene. The method has been employed to introduce through an α-linkage, an α-aminopentanoic acid chain at the anomeric carbon of β-D-C-gentiobiose to give a totally artificial glycosyl α-amino acid of a disaccharide. This compound represents the isostere of the α-linked glycosylasparagine moiety of the natural glycopeptide nephritogenoside.