Carbohydrate research

O-Alkylation at the anomeric centre for the stereoselective synthesis of Kdo-α-glycosides

A Esswein, H Rembold, RR Schmidt

Index: Esswein, Angelika; Rembold, Hansjoerg; Schmidt, Richard R. Carbohydrate Research, 1990 , vol. 200, p. 287 - 305

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Citation Number: 26

Abstract

Abstract O-Alkylation at the anomeric centre of the dianion of 4, 5: 7, 8-di-O-cyclohexylidene- 3-deoxy-N-methyl-α-d-manno-octulopyranosonamide (1) with several triflates led diastereoselectively to the α-glycosides. In this way, lipopolysaccharide building-blocks containing α-Kdo-(2→ 6)-GlcN and α-Kdo-(2→ 6)-β-GlcN-(1→ 6)-GlcN moieties were obtained and deployed in the synthesis of decyl 4, 5, 7, 8-tetra-O-acetyl-3-deoxy-N-methyl ...