A comparative study of the influence of some protecting groups on the reactivity of D-glucosamine acceptors with a galactofuranosyl donor

被引：21

作者：

Bohn, Maria L.

Colombo, Maria I.

Stortz, Carlos A.

Ruveda, Edmundo A.

机构：

[1] Univ Nacl Rosario, CONICET, Fac Ciencias Bioquim & Farmaceut, Inst Quim Organ & Sintesis, RA-2000 Rosario, Argentina

[2] Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, CIHIDECAR, RA-1428 Buenos Aires, DF, Argentina

来源：

CARBOHYDRATE RESEARCH | 2006年 / 341卷 / 09期

关键词：

glucosamine acceptors; N-dimethylmaleoyl group; galactofuranosyl donor; competitive glycosylations; DFT;

D O I：

10.1016/j.carres.2006.03.030

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：

Competitive glycosylation experiments with a galactofuranosyl trichloroacetimidate donor were performed with glucosamine acceptors having a free 4-OH group and carrying different protecting groups at N-2, O-3, and O-6. The most reactive acceptor is the N-dimethylmaleimido 3,6-di-O-benzylated derivative (6c), which reacts even faster than the oxazolidinone 1a. Molecular orbital calculations have helped to rationalize these experimental facts in terms of a hard-hard reaction occurring between the donor and the acceptor. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：1096 / 1104

页数：9

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