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標題: Selective S‐Deacetylation of Functionalized Thioacetates Catalyzed by Dy(OTf)3
作者: Jiun‐Rung Guo
Hsin‐Yi Huang
Yi‐Ling Yan
Prof. Chien‐Fu Liang
關鍵字: deacetylation;dysprosium;lanthanides;sulfur;synthetic methods
Project: ASIAN JOURNAL OF ORGANIC CHEMISTRY, Volume 7, Issue 1 January 2018, Pages 179-188
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.
DOI: 10.1002/ajoc.201700481
Appears in Collections:化學系所

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