Solvent Effects in the Nucleophilic Substitutions of Tetrahydropyran Acetals Promoted by Trimethylsilyl Trifluoromethanesulfonate: Trichloroethylene as Solvent for Stereoselective C- and O-Glycosylations

被引：31

作者：

Kendale, Joanna C. ^{[1
]}

Valentin, Elizabeth M. ^{[1
]}

Woerpel, K. A. ^{[1
]}

机构：

[1] NYU, Dept Chem, New York, NY 10003 USA

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 14期

基金：

美国国家卫生研究院;

关键词：

OXOCARBENIUM IONS; STEREOCHEMICAL CONTROL; IONIZING POWER; DONORS; CONSTRUCTION; SCALE; DIASTEREOSELECTIVITY; THIOGLYCOSIDES; INTERMEDIATE; GLYCOSIDES;

D O I：

10.1021/ol501471c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The selectivities of nucleophilic substitution reactions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate depend upon the reaction solvent. Polar solvents favor the formation of S(N)1 products, while nonpolar solvents favor S(N)2 products. Trichloroethylene was identified as the solvent most likely to give S(N)2 products in both C- and O-glycosylation reactions.

引用

页码：3684 / 3687

页数：4

共 58 条

[41]

Mohammad M., 1970, J PHYS CHEM-US, V74, P1153

[42]

Nakajima A., 1974, Journal of Luminescence, V8, P266, DOI 10.1016/0022-2313(74)90062-3

[43] 13C NMR Spectroscopy for the Quantitative Determination of Compound Ratios and Polymer End Groups [J].