O-glycoside synthesis under neutral conditions in concentrated solutions of 
LiClO4 in organic solvents employing O-acyl-protected glycosyl donors

Bohm, G; Waldmann, Herbert

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O-glycoside synthesis under neutral conditions in concentrated solutions of LiClO4 in organic solvents employing O-acyl-protected glycosyl donors

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Waldmann, Herbert
Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society;

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Citation

Bohm, G., & Waldmann, H. (1996). O-glycoside synthesis under neutral conditions in concentrated solutions of LiClO4 in organic solvents employing O-acyl-protected glycosyl donors. LIEBIGS ANNALEN, (4), 621-625.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-9CBD-B

Abstract

O-Glycosides of pivaloyl-protected glucose can be synthesized under neutral conditions in moderate yields by employing the pivaloylated beta-glucosyl fluoride 2d and the respective beta-benzyl phosphate 2e as glycosyl donors and 1 M solutions of LiClO4 in CH2Cl2 or CHCl3 as reaction media, acetyl-protected alpha- or beta-configured glucosyl trichloroacetimidates la and Ib were converted into the orthoesters 6 which were isolated in moderate to high yields. Under these conditions, acetyl-protected glycosyl phosphates, acetyl- or pivaloyl-protected glycosyl bromides and O-pivaloylated glycosyl trichloroacetimidates were not converted to the desired O-glycosides.