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三氟甲磺酸三甲基硅酯促进的四氢吡喃缩醛亲核取代反应中的溶剂效应：以三氯乙烯为溶剂进行立体选择性C-和O-糖基化反应

Solvent effects in the nucleophilic substitutions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate: trichloroethylene as solvent for stereoselective C- and O-glycosylations.

作者信息

Kendale Joanna C, Valentín Elizabeth M, Woerpel K A

机构信息

Department of Chemistry, New York University , New York, New York 10003, United States.

出版信息

Org Lett. 2014 Jul 18;16(14):3684-7. doi: 10.1021/ol501471c. Epub 2014 Jul 3.

DOI:10.1021/ol501471c
PMID:24991982
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4334250/
Abstract

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.

摘要

三氟甲磺酸三甲基硅酯促进的四氢吡喃缩醛亲核取代反应的选择性取决于反应溶剂。极性溶剂有利于S(N)1产物的形成，而非极性溶剂有利于S(N)2产物的形成。三氯乙烯被确定为在C-和O-糖基化反应中最有可能生成S(N)2产物的溶剂。

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