54829-40-2Relevant academic research and scientific papers
Ynamide-Mediated Thioester Synthesis
Wang, Xuewei,Zhao, Yongli,Yang, Jinhua,Li, Yanxi,Luo, Ying,Xu, Mengyao,Zhao, Junfeng
, p. 18265 - 18277 (2021/12/17)
A novel ynamide-mediated thioester synthesis strategy was developed. Importantly, no detectable racemization was observed for the thioesterifications of carboxylic acids containing an α-chiral center, enabling it to be useful for the synthesis of peptide thioester, which is the key component of native chemical ligation. It is worth mentioning that amino acid side chain functional groups such as -OH and indole -NH are compatible with the reaction conditions, rendering their protection unnecessary. Moreover, this method was also amenable to selenoesters.
A Mild Method for Access to α-Substituted Dithiomalonates through C-Thiocarbonylation of Thioester: Synthesis of Mesoionic Insecticides
Di, Huiming,Jin, Hui,Ma, Yanrong,Ryu, Do Hyun,Wang, Xiaochen,Yang, Xinyue,Zhang, Lixin
supporting information, p. 3201 - 3206 (2021/05/31)
An efficient method for targeting a variety of symmetrical and asymmetrical α-substituted dithiomalonates (DTMs) is described, utilizing 1H-imidazole-1-carbothioates as reactive acylating agents and MgBr2?OEt2/DBU or LiHMDS for soft or hard enolization conditions of thioesters, respectively. The utility of this methodology was demonstrated through the synthesis of the pyridopyrimidine mesoionic insecticides: triflumezopyrim and dicloromezotiaz. (Figure presented.).
Processes for forming amide bonds and compositions related thereto
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Page/Page column 32, (2015/01/07)
The disclosure relates to methods for producing amide bonds and reagents related thereto. In some embodiments, the disclosure relates to methods of producing an amide comprising mixing an O-silylated thionoester and an amine under conditions such that an amide is formed. In another embodiment, the disclosure relates to mixing a thiolacid, a silylating agent, and an amine under conditions such that an amide is formed.
Ligand exchange reaction of sulfoxides in organic synthesis: A versatile procedure for one-carbon homologation of methylesters to esters, thioesters, carboxylic acids and amides
Satoh, Tsuyoshi,Unno, Hideaki,Mizu, Yasuhiro,Hayashi, Yasumasa
, p. 7843 - 7854 (2007/10/03)
A novel two-step procedure for one-carbon homologation of methylesters to esters, thioesters, carboxylic acids and amides is described. Methylesters are reacted with lithium carbanion of chloromethyl phenyl sulfoxide to give α-chloro α-sulfinyl ketones in 70 to 90% yields. Potassium enolate of the α-chloro α-sulfinyl ketone was treated with tert-butyllithium at -78°C to give alkynolate via alkylidene carbenoid. This intermediate was treated with alcohols, thioles, 5% aqueous NaOH, and amine hydrochlorides to afford one-carbon homologated esters, thioesters, carboxylic acids and amides, respectively, in good to excellent yields.
Nucleophilic and Electrophilic Mercaptanylations via 2-(Trimethylsilyl)ethanethiol-Derived Reagents
Anderson, M.B.,Ranasinghe, M.G.,Palmer, J.T.,Fuchs, P.L.
, p. 3125 - 3127 (2007/10/02)
2-(Trimethylsilyl)ethanethiol reacts with carboxylic acids, alkyl halides, epoxides, and enones to provide acyl- and alkyl-substituted 2-(trimethylsilyl)ethyl sulfides.Electrophilic mercaptanylation is effected by a thiol-sulfonate reagent derived from 2-(trimethylsilyl)ethanethiol.
NEW SYNTHETIC 'TRICKS'. ADVANTAGES OF USING TRIETHYLPHOSPHINE IN SOME PHOSPHORUS-BASED REACTIONS
Urpi, Felix,Vilarrasa, Jaume
, p. 4623 - 4624 (2007/10/02)
It is shown that Et3P can advantageously replace Ph3P, Bu3P, and other P(III) reagents in phosphazene reactions (amide and phthalimide formation) and disulphide-cleavage-based reactions (reduction of disulphides, thioester formation, and oxime hydrolysis).
COBALT CARBONYL CATALYZED REACTIONS OF DISULFIDES: CARBONYLATION TO THIOESTERS AND DESULFURIZATION TO SULFIDES.
Antebi, Shlomo,Alper, Howard
, p. 2609 - 2612 (2007/10/02)
Aromatic and benzylic disulfides react with carbon monoxide and a catalytic amount of cobalt carbonyl to give thioesters and carbonyl sulfide, while the presence of t-butyl peroxide results in the formation of sulfides in high yields.
An Odorless Preparative Method of Sulfides and Thiocarboxylic S-Esters Using 3-(Alkylthio)-1,2-benzisothiazole 1,1-Dioxide
Yamada, Hiroyuki,Kinoshita, Hideki,Inomata, Katsuhiko,Kotake, Hiroshi
, p. 949 - 950 (2007/10/02)
It was found that sodium salt of 1,2-benzisothiazole-3(2H)-thione 1,1-dioxide (thiosaccharin) readily reacted with alkyl halide affording 3-(alkylthio)-1,2-benzisothiazole 1,1-dioxide (3).Treatment of 3 with piperidine produces the corresponding alkanethiol in situ quantitatively and subsequent treatment with various electrophiles gives the corresponding sulfides and thiocarboxylic S-esters in good yields.
