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Stereochemical analysis of D-glucopyranosyl-sulfoxides via a combined NMR, molecular modeling and X-ray crystallographic approach

被引：20
作者：
Buist, PH
Behrouzian, B
MacIsaac, KD
Cassel, S
Rollin, P
Imberty, A
Gautier, C
Pérez, S
Genix, P
机构：
[1] Carleton Univ, Ottawa Carleton Chem Inst, Dept Chem, Ottawa, ON K1S 5B6, Canada
[2] Univ Orleans, ICOA, F-45067 Orleans, France
[3] Univ Grenoble 1, CNRS, CERMAV, F-38041 Grenoble, France
[4] Rhone Poulenc Agrochim, F-69009 Lyon, France
来源：
TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 15期
基金：
加拿大自然科学与工程研究理事会;
关键词：
D O I：
10.1016/S0957-4166(99)00294-3
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
(S)-alpha-Methoxyphenylacetic acid (MPAA) was used as an NMR shift reagent in combination with molecular modeling to predict the absolute configuration of a representative epimeric pair of glucopyranosyl sulfoxides. The correctness of this assignment was confirmed by X-ray crystallographic examination of one of the epimers, 3a1. The crystal structure of ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-beta-D-glucopyranoside S-oxide monohydrate 3a1 was solved by direct methods and was shown to bear the (R)-configuration at the sulfinyl center in accordance with our prediction. Furthermore, the conformation of 3a1 in the solid state was found to be remarkably similar to that predicted by molecular mechanics calculations. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：2881 / 2889
页数：9
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