Practical synthesis of the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-d-glucosides of Fmoc-serine and Fmoc-threonine and their benzyl esters Original Research Article

Mercuric bromide-promoted glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-d-glucopyranosyl chloride in refluxing 1,2-dichloroethane gave the corresponding β-glycosides in good yields (64 and 62%, respectively). Direct coupling of the commercially available Fmoc-Ser-OH and Fmoc-Thr-OH carboxylic acids under similar conditions gave the corresponding β-glycosides, possessing free carboxyl groups, in moderate yields (50 and 40%, respectively).