13286-32-3Relevant academic research and scientific papers
A New, Efficient Synthesis of Thioloesters
Nowicki, Tomasz,Markowska, Anna,Kielbasinski, Piotr,Mikolajczyk, Marian
, p. 305 - 308 (1986)
The reaction between phosphorothioic and thiocarboxylic acids and O-alkyl-N,N-dicyclohexylisoureas has been found to give the corresponding phosphorothiolates and thiolocarboxylates in high yields (65-95percent), providing a new method for the thiophosphorylation and thiocarboxylation of alcohols.
Reactions of Disulfides with Silyl Phosphites to Generate Thiophosphates Under Neat Conditions
Zhan, Zhen,Yang, Zhongzhen,Ma, Dena,Zhang, Hao,Shi, Yuesen,Wang, Qiantao,Deng, Yong,Hai, Li,Wu, Yong
, p. 1426 - 1431 (2018)
An efficient procedure for the synthesis of thiophosphates is described. Without using any metallic catalyst or base, the direct sulfur–phosphorus coupling reaction of disulfides and dialkyl trimethylsilyl phosphite (DTSP) was carried out under solvent-fr
A convenient method for the synthesis of phosphorothioates and their anticholinesterase activites
Kaboudin, Babak,Emadi, Saeed,Norouzi, Hamid
, p. 585 - 590 (2004)
A simple, efficient, and general method has been developed for the synthesis of phosphorothioates through a one-pot reaction of alkyl halides with the mixture of diethyl phosphite in the presence of NH4OAc/S/CaO under solvent-free conditions. T
Easy access to phosphonothioates.
Renard, Pierre-Yves,Schwebel, Herve,Vayron, Philippe,Josien, Ludovic,Valleix, Alain,Mioskowski, Charles
, p. 2910 - 2916 (2002)
A new and particularly mild method for the formation of phosphorus-sulfur bonds has been achieved through base-catalyzed addition of thiocyanate to the corresponding H-phosphine oxide, phosphinate, or phosphonate. This reaction procedure offers many advantages: the use as starting material of a stable and not oxygen-sensitive phosphorus(v) species, particularly mild and nonaqueous reaction conditions and workup (a pivotal point for these sensitive phosphonothioates), and, through optimized access to thiocyanates, a wider scope of substrates. This method has been applied to achieve the synthesis of substrate analogues for the study of antibody-catalyzed hydrolysis of acetylcholinesterase inhibitor PhX (11).
Sulfonyl-Promoted Michaelis-Arbuzov-Type Reaction: An Approach to S/Se-P Bonds
Rather, Suhail A.,Bhat, Mohammad Yaqoob,Hussain, Feroze,Ahmed, Qazi Naveed
, p. 13644 - 13663 (2021/10/01)
By facilitating the chemical conversion of thiols to thiosulfonates, phosphoramidite/phosphite bearing sp3-hybridized carbon serves as an ideal coupling material to forge new connections at room temperature. In this work, a functional group-induced, additive-free, novel, S-P bond-forming approach is presented. This protocol exhibits good functional group tolerance with wide applications that include phosphorylation of cysteine derivatives, development of a one-pot approach to mixed unsymmetrical thiophosphonates, and extension of the concept to different Se-P bonds. Meticulously, our reaction also generated a S-P bond against cyclic 1,2-dithiane-1-dioxide in a byproduct-free manner. These Michaelis-Arbuzov-type reactions are easy to conduct, work efficiently in a reduced reaction time, and are applicable to gram-scale preparation as well.
Photoinduced Decarboxylative Phosphorothiolation of N-Hydroxyphthalimide Esters
Guo, Yu,Luo, Ying,Mu, Shiqiang,Xu, Jian,Song, Qiuling
, p. 6729 - 6734 (2021/09/11)
A visible-light-induced protocol for the synthesis of phosphorothioates is developed by employing the Ir-catalyzed decarboxylative phosphorothiolation of N-hydroxyphthalimide esters. This novel synthesis method utilizes carboxylic acids as raw material, which is stable, cheap, and commercially available. Scope studies show that this reaction has good compatibility of functional groups. Notably, both the synthesis of steric hindrance phosphorothioates and the later modification of some bioactive compounds are successfully achieved.
Electrochemically driven synthesis of phosphorothioates from trialkyl phosphites and aryl thiols
Guo, Xiaqun,Li, Meichao,Liu, Xin,Shen, Zhenlu,Shi, Shuxian,Wu, Zengzhi,Zhao, Lingmin
, (2021/06/25)
A facile and elegant protocol for synthesis of phosphorothioates from trialkyl phosphites and aryl thiols via indirect electrochemical oxidation mediated by KI has been successfully developed. KI as a redox mediator, enabled the reaction of trialkyl phosp
Trichloroisocyanuric acid-promoted thiolation of phosphites by thiols
Chen, Yingying,Li, Meichao,Gong, Zhangshui,Shen, Zhenlu
, p. 19 - 27 (2020/08/06)
A simple and convenient method for the synthesis of thiophosphates by coupling of phosphites with thiols under mild conditions has been developed. The reactions were promoted by trichloroisocyanuric acid (TCCA) and were carried out at room temperature in
Synthetic method of thiophosphate compound
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Paragraph 0063-0064, (2020/05/30)
The invention discloses a synthetic method of a phosphorothioate compound. The preparation method comprises the following steps: with thiol as a reaction substrate and trichloroisocyanuric acid (TCCA)as an accelerant, reacting the reaction substrate and the accelerant in an organic solvent at normal temperature and normal pressure for 10-20 minutes, then adding phosphite triester, continuing reacting for 10-20 minutes, and after the reaction is finished, carrying out separation treatment to obtain the phosphorothioate compound. According to the synthesis method disclosed by the invention, thereaction is carried out at normal temperature and normal pressure without special requirements; reaction time is short; and reaction substrate universality is good.
A Robust Methodology for the Synthesis of Phosphorothioates, Phosphinothioates and Phosphonothioates
Jones, David J.,O'Leary, Eileen M.,O'Sullivan, Timothy P.
supporting information, (2020/03/27)
A robust methodology for the synthesis of phosphorothioates, phosphinothioates and phosphonothioates, including those bearing low molecular weight S-alkyl side-chains, is presented. Application of the “caesium effect” in conjunction with the disulfide 3,3’-dithiobis(propionitrile), which acts as a shelf-stable sulfur source, avoids recourse to malodorous alkanethiols and toxic P?Cl precursors. A diverse range of sulfur-containing organophosphorus targets, including phosphorus-based heterocycles, may be prepared in consistently high yields. This chemistry also provides ready access to the corresponding DBU salts which are potential substrates for Pd-catalysed coupling reactions. (Figure presented.).
