Selective S‐Deacetylation of Functionalized Thioacetates Catalyzed by Dy(OTf)₃

Abstract

The dysprosium(III)-trifluoromethanesulfonate-catalyzed S-deacetylation and selective S-deacetylation reactions of functionalized thioesters could be tuned by changing the reactionm edium or through the inclusiono fa dditives. In this study,t he deprotection of thioacetates by using catalytic amounts of Dy(OTf) 3 under mild heating resultedi n high yields of the free thiols without the formation of disulfide byproducts, whilst the selective S-deacetylation reaction by using ac ombination of catalytic amounts of Dy(OTf) 3 and NaHCO 3 afforded the products in moderate-to-excellent yields. Moreover,g lycosyl 1-thioacetate was selectively S-deacetylated at the anomeric position in ac o-solvent system. Notably,D y(OTf) 3 is an environmentally friendly catalyst, and ar ecycling strategy was successfully employed for the S-deacetylation reaction.

Sequential Ytterbium(III) Triflate Catalyzed One‐Pot Three‐Component Thia‐Michael Addition

“…This low yield may be attributed to undesired products that are generated from the ring opening of N ‐phenylmaleimide ( 4 f ) . On the basis of our previous work, we assumed that a cosolvent system may suppress the generation of the ring‐opened byproduct. Thus, Michael acceptor 4 f was treated in MeOH/CH 2 Cl 2 as a cosolvent system, which led to an increase in the yield of the desired product 5 f to 41 % and a decrease in the yield of the byproduct 4 g to 31 %…”

“…We recently performed the selective S ‐deacetylation of thioacetates by using dysprosium(III) triflate . On the basis of our experiences with catalytic S ‐transesterifications and to comprehensively study the catalytic applications of lanthanide(III) triflates in various organic transformations, we herein have used a lanthanide(III) triflate as a dual catalyst in the one‐pot sequential S ‐deacetylation and thia‐Michael addition reactions of three components, that is, an organic halide, potassium thioacetate, and a Michael acceptor (Scheme c).…”

In vitro and in vivo antiplasmodial evaluation of sugar-modified nucleoside analogues

“…Nucleoside derivatives 1–6 17 , 10 16 and 19 18 , naphtylmethylmercaptane 27c 29 , Fmoc-cysteine derivative 27d 17 , 1-thiosugars 27f-i 30 , adenosine-4’-exomethylene 28 16 , uridine-2’-exomethylene 29 31 , uridine-3’-exomethylene 30 16 and 5-methyluridine-3’-exomethylene 31 16 were prepared according to literature procedures. 2,2-Dimethoxy-2-phenylacetophenone (DPAP), n -butyl mercaptane 27b , and MesNa 27e were purchased from Sigma-Aldrich Chemical Co. and used without further purification.…”

From dithiocarbamates to branched dithiocarbazates: Compounds with potent antischistosomal activity

“…The spectroscopic data are comparable to the published data (CDCl 3 ). [ 46 ] MS (ESI−): m/z (%) = 168 (100, [M−H] − ).…”