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

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.