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

被引：27

作者：

Carvalho, I

Scheuerl, SL

Kartha, KPR

Field, RA

机构：

[1] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland

[2] Univ St Andrews, Ctr Biomol Sci, St Andrews KY16 9ST, Fife, Scotland

[3] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, BR-14040930 Ribeirao Preto, Brazil

[4] Univ E Anglia, Sch Chem Sci & Pharm, Ctr Carbohydrate Chem, Norwich NR4 7TJ, Norfolk, England

来源：

CARBOHYDRATE RESEARCH | 2003年 / 338卷 / 10期

基金：

巴西圣保罗研究基金会; 英国医学研究理事会;

关键词：

serine; threonine; benzyl ester; free carboxylic acid; mercuric bromide; glycosylation;

D O I：

10.1016/S0008-6215(03)00071-5

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Mercuric bromide-promoted glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with 2-acetamido-2-deoxy-3,4,6-tri-O-acetyla-alpha-D-glucopyranosyl chloride in refluxing 1,2-dichloroethane gave the corresponding P-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). (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：1039 / 1043

页数：5

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