当前位置: X-MOL 学术Asian J. Org. Chem. › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
Selective S‐Deacetylation of Functionalized Thioacetates Catalyzed by Dy(OTf)3
Asian Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2017-11-09 , DOI: 10.1002/ajoc.201700481
Jiun-Rung Guo,Hsin-Yi Huang,Yi-Ling Yan,Chien-Fu Liang

The dysprosium(III)‐trifluoromethanesulfonate‐catalyzed S‐deacetylation and selective S‐deacetylation reactions of functionalized thioesters could be tuned by changing the reaction medium or through the inclusion of additives. In this study, the deprotection of thioacetates by using catalytic amounts of Dy(OTf)3 under mild heating resulted in high yields of the free thiols without the formation of disulfide byproducts, whilst the selective S‐deacetylation reaction by using a combination of catalytic amounts of Dy(OTf)3 and NaHCO3 afforded the products in moderate‐to‐excellent yields. Moreover, glycosyl 1‐thioacetate was selectively S‐deacetylated at the anomeric position in a co‐solvent system. Notably, Dy(OTf)3 is an environmentally friendly catalyst, and a recycling strategy was successfully employed for the S‐deacetylation reaction.

中文翻译:

Dy(OTf)3催化的功能化硫代乙酸酯的选择性S-脱乙酰化

可以通过改变反应介质或添加添加剂来调节tri(III)-三氟甲磺酸dy催化的功能化硫酯的S-脱乙酰化和选择性S-脱乙酰化反应。在这项研究中,通过在适度加热下使用催化量的Dy(OTf)3对硫代乙酸酯进行脱保护,可得到高产率的游离硫醇,而不会形成二硫键副产物,而通过结合催化量进行选择性S-脱乙酰化反应Dy(OTf)3和NaHCO 3的收率中等至优异。此外,在共溶剂体系中的异头位置,将1-硫代乙酸糖基酯选择性地S-去乙酰化。值得注意的是,Dy(OTf)3 是一种环境友好的催化剂,S-脱乙酰化反应已成功采用了回收策略。
更新日期:2017-11-09
down
wechat
bug