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Practical stereoselective synthesis of alpha-linked C-glucosamine propionic acid esters: conversion to GLA-60
Takanori Wakabayashi1, Masao Shiozaki, Shin-ichi Kurakata
1Exploratory Chemistry Research Laboratories, Sankyo Co. Ltd., Hiromachi 1-2-58, Shinagawa-ku, Tokyo 140-8710, Japan.
Carbohydrate Research
|January 30, 2002
Abstract:
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.