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. © 2001 The Royal Society of Chemistry.

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

DONDONI, Alessandro;GIOVANNINI, Pier Paolo;MARRA, Alberto
2001

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-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. © 2001 The Royal Society of Chemistry.
2001
Dondoni, Alessandro; Giovannini, Pier Paolo; Marra, Alberto
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11392/1205658
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