N α-Dmc protected amino acid aglycones: versatile hydrogenolysis stable acceptors for O-glycosylation

[Display omitted] N α-(4,4-Dimethyl-2,6-dioxocyclohexylidenemethylene) (Dmc) protected l-serine, l-threonine and l-homoserine have been prepared as tert-butyl esters in excellent yields. These hydrogenolysis stable acceptors underwent efficient α- O-glycosylation with an l-fucopyranosyl bromide dono...

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Bibliographic Details
Published in:Tetrahedron letters 2005-03, Vol.46 (10), p.1703-1706
Main Authors: Kellam, Barrie, Ward, Paul A., Abdul Rahim, Aisyah S., Chhabra, Siri Ram
Format: Article
Language:English
Subjects:
Amino acids and derivatives
Glycosylation
Protecting groups
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Summary:[Display omitted] N α-(4,4-Dimethyl-2,6-dioxocyclohexylidenemethylene) (Dmc) protected l-serine, l-threonine and l-homoserine have been prepared as tert-butyl esters in excellent yields. These hydrogenolysis stable acceptors underwent efficient α- O-glycosylation with an l-fucopyranosyl bromide donor and also allowed convenient protecting group manipulations to ultimately deliver novel glycoamino acid building blocks suitable for Fmoc based solid-phase glycopeptide synthesis.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.01.055