Practical stereoselective synthesis of alpha-linked C-glucosamine propionic acid esters: conversion to GLA-60 derivatives.

Carbohydr Res

Exploratory Chemistry Research Laboratories, Sankyo Co. Ltd., Hiromachi 1-2-58, Shinagawa-ku, Tokyo 140-8710, Japan.

Published: February 2002

Radical C-glycosylation of glucosamine derivatives by acrylic acid esters gave the corresponding 3-(alpha-C-glucosyl)-propionate derivatives in moderate yields. One of them was used as a versatile synthon for GLA-60 derivatives. However, the biological activity of these compounds as LPS-antagonists was disappointing.

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http://dx.doi.org/10.1016/s0008-6215(01)00290-7DOI Listing

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