57830-63-4

Upstream product

• 106-45-6 para-thiocresol 
• 102-92-1 Cinnamoyl chloride 
• 17671-92-0 subsituted benzenethiol 
• 101349-79-5 2-phenylvinyl iodide 
• 106871-53-8 2-(p-tolylthio)-2-oxoacetic acid 
• 536-74-3 phenylacetylene 
• 201230-82-2 carbon monoxide 
• 621-82-9 Cinnamic acid 
• 103-19-5 di(p-tolyl) disulfide 
• 328012-09-5 (E)-1-(1H-benzo[d][1,2,3]triazol-1-yl)-3-phenylprop-2-en-1-one 
• 933-00-6 p-methylbenzenesulfenyl chloride 
• 102-92-1 cinnamoyl chloride 

Downstream Products

• 117411-09-3 3-phenylpropanoyl-CoA 
• 30801-99-1 cinnamoyl-CoA 
• 795-47-1 (E)-diphenyl(styryl)phosphine oxide 
• 893445-49-3 [Pt(P(C₆H₅)3)2(CH₃C₆H₄SC(O)CHCHC₆H₅)] 
• 893445-50-6 trans-[Pt(SC₆H₄Me-p)(PPh₃)2(C(O)CH=CHPh)] 

Relevant academic research and scientific papers

Ligand-Controlled Regiodivergent Thiocarbonylation of Alkynes toward Linear and Branched α,β-Unsaturated Thioesters

Thiocarbonylation of alkynes offers an ideal procedure for the synthesis of unsaturated thioesters. A robust ligand-controlled regioselective thiocarbonylation of alkynes is developed. Utilizing boronic acid and 5-chlorosalicylic acid as the acid additive to in situ form 5-chloroborosalicylic acid (5-Cl-BSA), and bis(2-diphenylphosphinophenyl)ether (DPEphos) as the ligand, linear α,β-unsaturated thioesters were produced in a straightforward manner. Switching the ligand to tri(2-furyl)phosphine can turn the reaction selectivity to give branched products. Remarkably, this approach also represents the first example on thiocarbonylation of internal alkynes.

Controllable phosphorylation of thioesters: Selective synthesis of aryl and benzyl phosphoryl compounds

The controllable phosphorylations of thioesters were developed. When the reaction was catalyzed by a palladium catalyst, aryl or alkenyl phosphoryl compounds were generated through decarbonylative coupling, while the benzyl phosphoryl compounds were produced through deoxygenative coupling when the reaction was carried out in the presence of only a base.

Metal-free thioesterification of amides generating acyl thioesters

A base-initiated thioesterification of amides with various thiols is reported. This reaction can take place efficiently under metal-free and air-atmospheric conditions, and provides a facile and practically useful approach to the synthesis of valuable acy

Oxalic Acid Monothioester for Palladium-Catalyzed Decarboxylative Thiocarbonylation and Hydrothiocarbonylation

Oxalic acid monothioester (OAM), an easily accessible and storable reagent, was reported herein as a thioester synthetic equivalent for palladium-catalyzed decarboxylative thiocarbonylation of organohalides and hydrothiocarbonylation of unsaturated carbon-carbon bonds at room temperature with high chemo- and regioselectivity. The reaction is applicable to the synthesis of cysteine-derived thioesters, thus allowing chemical modification of cysteine-containing peptides. Decarboxylation of OAM proceeds through oxidative addition of Pd(0) to the acyl-S bond, which accounts for the very mild reaction conditions.

Method for producing thioesters by means of oxo thio acetic acid compounds

The invention provides a method for preparing thioesters from oxo thio acetic acid compounds. In the presence of a palladium catalyst, a phosphine ligand and an organic solvent, an oxo thio acetic acid compound is decarboxylated and then reacts with an ar

Uncovering the formation and selection of benzylmalonyl-CoA from the biosynthesis of splenocin and enterocin reveals a versatile way to introduce amino acids into polyketide carbon scaffolds

Selective modification of carbon scaffolds via biosynthetic engineering is important for polyketide structural diversification. Yet, this scope is currently restricted to simple aliphatic groups due to (1) limited variety of CoA-linked extender units, which lack aromatic structures and chemical reactivity, and (2) narrow acyltransferase (AT) specificity, which is limited to aliphatic CoA-linked extender units. In this report, we uncovered and characterized the first aromatic CoA-linked extender unit benzylmalonyl-CoA from the biosynthetic pathways of splenocin and enterocin in Streptomyces sp. CNQ431. Its synthesis employs a deamination/reductive carboxylation strategy to convert phenylalanine into benzylmalonyl-CoA, providing a link between amino acid and CoA-linked extender unit synthesis. By characterization of its selection, we further validated that AT domains of splenocin, and antimycin polyketide synthases are able to select this extender unit to introduce the phenyl group into their dilactone scaffolds. The biosynthetic machinery involved in the formation of this extender unit is highly versatile and can be potentially tailored for tyrosine, histidine and aspartic acid. The disclosed aromatic extender unit, amino acid-oriented synthetic pathway, and aromatic-selective AT domains provides a systematic breakthrough toward current knowledge of polyketide extender unit formation and selection, and also opens a route for further engineering of polyketide carbon scaffolds using amino acids.

Convenient and efficient synthesis of thiol esters using zinc oxide as a heterogeneous and eco-friendly catalyst

A catalytic method was developed to synthesize thiol esters from the reaction of acyl chlorides and thiols using zinc oxide as a catalyst under solvent-free conditions at room temperature. Mild reaction conditions, short reaction time, excellent yields of products and recyclability of the catalyst are noteworthy features of this methodology. CSIRO 2008.

An efficient synthesis of α,β-unsaturated thiol esters

α,β-Unsaturated thiol esters were synthesised conveniently from samarium thiolates and α,β-unsaturated N-acylbenzotriazoles under mild conditions with good to excellent yields.

Ketone synthesis under neutral conditions. Cu(I) diphenylphosphinate-mediated, palladium-catalyzed coupling of thiol esters and organostannanes

(Matrix presented) A versatile approach to ketone synthesis is described. The reaction relies on the palladium-catalyzed, copper diphenylphosphinate-mediated coupling of thiol esters with organostannanes under neutral reaction conditions. This reaction complements the previously described coupling of thiol esters with boronic acids that used dual thiophilic-borophilic activation methodology.

A stereoselective synthetic route to (E)-α,β-unsaturated thioesters

Terminal alkynes 1 react with Cp2Zr(H)Cl (Cp = η5-C5H5) and CO to give acylzirconocene chloride derivatives 2, which are trapped with arylsulfenyl chlorides to afford (E)-α,β-unsaturated thioesters.