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Selective S‐Deacetylation of Functionalized Thioacetates Catalyzed by Dy(OTf) 3
Author(s) -
Guo JiunRung,
Huang HsinYi,
Yan YiLing,
Liang ChienFu
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700481
Subject(s) - chemistry , catalysis , acetylation , trifluoromethanesulfonate , glycosyl , dysprosium , anomer , organic chemistry , chemoselectivity , polymer chemistry , solvent , halide , combinatorial chemistry , medicinal chemistry , inorganic chemistry , biochemistry , gene
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 NaHCO 3 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.