Details

Autor(en) / Beteiligte

• Lee, Ho Huat
• Baptista, Jose A. B
• Krepinsky, Jiri J

Titel

Syntheses of model oligosaccharides of biological significance. XI. A short synthesis of fucosylated chitobiosides, also bound to asparagine in a synthon (as in N-linked glycoproteins)

Ist Teil von

• Canadian journal of chemistry, 1990-06, Vol.68 (6), p.953-957

Ort / Verlag

Ottawa, Canada: NRC Research Press

Erscheinungsjahr

1990

Quelle

EZB Electronic Journals Library

Beschreibungen/Notizen

• We describe a simple and efficient method for the preparation of the trisaccharide GlcNAc(β1-4)-[Fuc(α 1-6)-]GlcNAc(β 1-) ( 1 ) and of the protected form of GlcNAc(β 1-4)-[Fuc(α 1-6)-]GlcNAc(β1-Asn) ( 2 ). The key intermediate is benzyl 4,6-benzylidene chitobioside 5 giving the desired trisaccharide by insitu anomerization-glycosylation reaction with 2,3,4-tribenzylfucosyl bromide. The benzyl glycoside in the trisaccharide 6 has been replaced by acetate and then bromine; this glycosylating agent was used to prepare methyl and 8-methoxycarbonyloctyl glycosides as well as isothiocyanate 12 , in a series of reactions. The latter compound gave, on reaction with 1-benzyl N-benzyloxycarbonyl- L -asparate, compound 13 (a protected derivative of 2 ), which should serve as a synthon for syntheses of glycopeptides. Keywords: glycopeptide, synthesis; oligosaccharide, synthesis; chitobiosides; fucosylated chitobiosides; N-linked oligosaccharides.