A simple, rapid and efficient protocol for the synthesis of methylthiomethyl esters under Swern oxidation conditions

Construction of 4‐(Methylthio)isochromenones Skeleton through Regioselective Intramolecular Cyclization of 2‐Alkynylbenzoate Mediated by DMSO/[D6]DMSO and SOCl2

“…Comparably, the application of DMSO/activating agents in organic transformations to introduce sulfur moiety has been less studied. Literature survey indicated that they can be used to introduce “CH 2 SMe” moiety into organic acid and indole with oxalyl chloride and TFAA “=SMe 2 ” moiety into thiatriazine and coumarin with TFAA and Ac 2 O, and “SMe” moiety with TFAA into indole . To the best of our knowledge, both DMSO and [D 6 ]DMSO have never been employed as a sulfur source for introduction of SMe or SCD 3 moiety to the biologically interesting isochromenone skeleton.…”

“…Comparably, the application of DMSO/activating agents in organic transformations to introduce sulfur moiety has been less studied. Literature survey indicated that they can be used to introduce "CH 2 SMe" moiety into organic acid [61] and indole [62] with oxalyl chloride [61] and TFAA [62] "=SMe 2 " moiety into thiatriazine [63] and coumarin [64] with TFAA [63] and Ac 2 O, [64] and "SMe" moiety with TFAA into indole. [65] To the best of our Scheme 1.…”

Preparation and odor characteristics of methylthiomethyl carboxylates

“…In our recent work, various transformations have been developed by using the combination reagents of sulfoxide and oxalyl halide, including sulfenyllactonization or chlorolactonization of alkenoic acids, bromination, sulfenylchlorination, or oxysulfenylation of alkenes, dehydration of primary amides or aldoximes, sulfenyletherification of alkenols, and the preparation of unsaturated lactones from 3‐alkenoic acids . During condition optimization for sulfenyllactonization of alkenoic acids with DMSO/(COCl) 2 , methylthiomethyl esters were observed to be formed when the reactions were carried out at ‐65℃, which was also reported by Jadhav and Ghosh . The reactions completed in 1‐2 h to produce methylthiomethyl esters in good yields.…”

Total Synthesis of Bistramide A and Its 36(Z) Isomers: Differential Effect on Cell Division, Differentiation, and Apoptosis

“…Saponification of the ester gave the corresponding carboxylic acid, which was oxidized under Swern conditions. At this stage, the α,β‐unsaturated ketone moiety was successfully put in place, yet a Pummerer rearrangement of the Swern intermediate also led to the formation of the (methylthio)methyl (MTM) ester of the acid functional group to provide 45 in good yield 31. The MTM ester facilitated the purification of the product and was subsequently deprotected with magnesium bromide, followed by EDCI‐mediated coupling of N ‐hydroxysuccinimide to provide the activated ester 3 in 40 % yield over four steps.…”