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Stereoselective synthesis of O-serinyl/threoninyl-2-acetamido-2-deoxy-α- or β-glycosides

✍ Scribed by Lajos Szabó; Jan Ramza; Courtney Langdon; Robin Polt

Publisher
Elsevier Science
Year
1995
Tongue
English
Weight
980 KB
Volume
274
Category
Article
ISSN
0008-6215

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✦ Synopsis

General glycosidation methodology has been developed which can selectively provide 2acetamido-2-deoxy-a-or /3-glycosides of fl-hydroxy-a-amino acid derivatives [glucopyranoside-(8, 43), galactopyranoside-(9, 13), mannopyranoside-( 10), lactoside analogs (11, 38) and 3-O-/3-galactopyranosyl-mannopyranoside (12)] stereoselectively in excellent yield from the highly nucleophilic a-imino esters (Schiff bases) of L-serine and L-threonine. Various glycosides were converted via their amino and acetamido derivatives to Fmoc-protected serinyl-or threoninyl-glycosides (24-28, 37, 41, 46) which are all suitable building blocks for the solid-phase synthesis of O-glycopeptides. Complete 1H-and 13C-NMR data are provided for all compounds.

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