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Practical synthesis of the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucosides of Fmoc-serine and Fmoc-threonine and their benzyl esters.

作者信息

Carvalho Ivone, Scheuerl Shona L, Ravindranathan Kartha K P, Field Robert A

机构信息

Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Brazil.

出版信息

Carbohydr Res. 2003 May 1;338(10):1039-43. doi: 10.1016/s0008-6215(03)00071-5.

DOI:10.1016/s0008-6215(03)00071-5
PMID:12706969
Abstract

Mercuric bromide-promoted glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-alpha-D-glucopyranosyl chloride in refluxing 1,2-dichloroethane gave the corresponding beta-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 beta-glycosides, possessing free carboxyl groups, in moderate yields (50 and 40%, respectively).

摘要

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