66303-55-7

Upstream product

• 108-98-5 thiophenol 
• 621-62-5 chloroacetaldehyde diethyl acetal 
• 109-92-2 ethyl vinyl ether 
• 931-59-9 benzenesulfenyl chloride 
• 5149-48-4 3-(phenylthio)-1,2-propanediol 
• 20451-53-0 Phenyl vinyl sulfoxide 
• 29279-23-0 Thiophenoxythioessigsaeure-S-aethylester 
• 64-19-7 acetic acid 
• 18666-68-7 vinyltriphenylsilane 
• 1125-26-4 dimethylphenylvinylsilane 
• 754-05-2 ethenyltrimethylsilane 
• 1822-73-7 phenylthioethylene 
• 699-12-7 2-(phenylthio)ethanol 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 

Downstream Products

• 80127-40-8 2-Phenylsulfanylmethyl-2,3-dihydro-pyran-4-one 
• 105126-60-1 2C₉H₁₂N₄S*H₂O₄S 
• 105126-76-9 2C₁₀H₁₄N₄S*H₂O₄S 
• 111248-45-4 2-(phenylthio)acetaldehyde cyanohydrin 
• 120966-88-3 (E)-(R)-6-Benzenesulfonyl-2-(tert-butyl-diphenyl-silanyloxy)-4-methyl-hex-4-en-3-one 
• 179670-28-1 trans-1-(phenylthio)-2-moroholinoethylene 
• 153823-27-9 (4-Methoxy-benzyl)-[2-phenylsulfanyl-eth-(E)-ylidene]-amine 
• 177416-12-5 phenyl 2,2-dideutero-2-hydroxyethyl sulfide 
• 85891-12-9 dimethyl 2-phenylthiomethylenemalonate 
• 483343-67-5 2-benzyl-6-(3,4-dimethoxy-benzyl)-3-morpholin-4-yl-7-phenylsulfanylmethyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-4-carboxylic acid ethyl ester 
• 483279-69-2 2-benzyl-6-[2-(3,4-dimethoxy-phenyl)-ethyl]-3-morpholin-4-yl-7-phenylsulfanylmethyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-4-carboxylic acid ethyl ester 
• 502145-86-0 5-methyl-2-phenylsulfanylmethyl-2,3-dihydropyran-4-one 
• 766546-74-1 2-hydroxy-1-phenylsulfanylheptan-4-one 
• 766546-98-9 (+/-)-3-hydroxy-4-phenylsulfanylbutyric acid ethyl ester 

Relevant academic research and scientific papers

Scalable asymmetric synthesis of a key fragment of Bcl-2/Bcl-xLinhibitors

The asymmetric synthesis of a 1,3-diamine building block for the elaboration of Bcl-2 and Bcl-xLprotein inhibitors is described through two key steps: (1) a highly diastereoselective aza-Reformatsky reaction, and (2) a chemoselective amination under Mitsunobu conditions. This synthetic sequence was also demonstrated to be successfully amenable to a large-scale synthesis. This journal is

Process for preparing sulfonamide compounds

The invention relates to a process for preparing sulfonamide compounds. The sulfonamide compound is an inhibitor of Bcl-2/Bcl-xL and is prepared from a compound (3R)-1-(3-(4-(4-(4-(3-(2-(4-chlorphenyl)-1-isopropyl-4-methylsulfonyl-5-methyl-1H-pyrrole-3-yl

PROCESS FOR PREPARING SULFONAMIDE COMPOUNDS

Provided are a process for preparing a sulfonamide compound which is an inhibitor of Bcl-2/Bcl-xL, including the compound (3R) -1- (3- (4- (4- (4- (3- (2- (4-chlorophenyl) -1-isopropyl-4-methylsulfonyl-5-methyl-1H-pyrrol-3-yl) -5-fluorophenyl) piperazine

New synthesis method of benzothiacyclopentadiene

The invention discloses a novel synthesis method of benzothiacyclopentadiene, and belongs to the technical field of synthesis. The method comprises the following steps that: under an alkaline condition, chloroacetaldehyde and thiophenol undergo a Williamson condensation reaction to obtain thiophenyl acetaldehyde, the thiophenyl acetaldehyde undergoes a cyclization and dehydration reaction with a dehydrating agent under an acidic condition, water is added, layering is performed, an organic layer is taken, and reduced pressure distillation is performed to obtain the target product benzothiacyclopentadiene. The method has the advantages of simple operation, mild reaction, easy realization of industrialization, and high product yield.

Multikilogram Synthesis of a Potent Dual Bcl-2/Bcl-xL Antagonist. 2. Manufacture of the 1,3-Diamine Moiety and Improvement of the Final Coupling Reaction

This paper describes the synthesis of kilogram quantities of the sulfonamide moiety 3 involved in a coupling reaction with acid moiety 2 to provide batches of drug candidate 1 for preclinical studies and first-in-human clinical trials. A first approach relying on a chiral separation furnished the desired enantiomer of 1,3-diamine 20, precursor of sulfonamide 3. An enantiomeric synthesis of 20 using the Ellman's chiral auxiliary coupled with an aza-Reformatsky reaction to control the stereochemistry is also discussed. Coupling conditions of the final step involving EDCI to provide 1 under a cGMP process are detailed. An alternative approach using N-(1-methanesulfonyl)benzotriazole is also presented.

2-(phenylthio)ethylidene derivatives as anti-Trypanosoma cruzi compounds: Structural design, synthesis and antiparasitic activity

Chagas disease is an illness caused by the protozoan parasite Trypanosoma cruzi. The current chemotherapy is based on benznidazole, and, in some countries, Nifurtimox, which is effective in the acute phase of the disease, but its efficacy in the chronic p

Direct access to α-sulfenylated amides/esters: Via sequential oxidative sulfenylation and C-C bond cleavage of 3-oxobutyric amides/esters

An efficient, environmentally benign and unprecedented synthesis of various α-sulfenylated amides/esters has been developed under oxygen atmosphere. The reaction shows good functional group tolerance and excellent chemo/regioselectivity. All the desired products were obtained in moderate to excellent yields, even on the gram scale. Practically, the related α-thiol Weinreb amide can be readily transferred to a series of prospective compounds, and selenium atom can be introduced to the α-sites of the amides in high yields.

Pummerer Cyclization Revisited: Unraveling of Acyl Oxonium Ion and Vinyl Sulfide Pathways

Two viable pathways (vinyl sulfide and acyl oxonium ion) for the Pummerer cyclization have been unraveled that expand the reaction scope and capabilities. Use of Br?nsted-enhanced Lewis acidity was key to realization of the vinyl sulfide pathway, whereas selective complexation of the sulfur lone pair facilitated the unprecedented acyl oxonium ion pathway. Preliminary mechanistic investigations support these hypotheses. A range of substrates have been explored to understand the reaction parameters.

A Stereoselective Synthesis of the Carbon Backbone of Phoslactomycin B

A convergent synthesis of the entire carbon framework of phoslactomycin B is disclosed. An initial route aimed to create the C-8 tetrasubstituted stereocentre through regioselective intermolecular coupling between an internal alkyne and an allyl silyl ether, adopting Trost's protocol, followed by [2,3] sigmatropic rearrangement. But this was not successful. In a second approach, a propargylic sulfide was rearranged to give an unsaturated ketone. This was then treated with lithio acetonitrile to create the C-8 stereocentre selectively. The C-4 and C-5 stereocentres were introduced by a non-Evans syn-aldol reaction using Crimmins's protocol. The C-9 and C-11 carbinol centres were created by asymmetric transfer hydrogenation. The (Z,Z)-diene moiety was introduced by partial reduction of a diyne following Hansen's modification of the Boland reduction reaction.

Borontribromide-mediated C-C bond formation in cyclic ketones: A transition metal free approach

Borontribromide (BBr3) is a well-known demethylating agent. The current investigation was focused on a new application of borontribromide as a C-C bond forming agent in cyclic ketones. In this study, borontribromide mediated C-C bond formation reactions of tetralones, chromenone, thiochromenone and indanones were explored. A methoxy group containing ketones showed selective C-C bond formation reaction instead of demethylation of the methoxy group. MM2 steric energy calculations for the final products showed that the reaction favored the formation of exo- or endo-cyclic double bond containing products, depending upon their low MM2 steric energy in a specific frame structure, as observed in X-ray crystallography. A comprehensive crystallographic and pi-stacking analysis of product 10a demonstrated the formation of 10a as an enantiomeric mixture, and its centre of inversion was stabilized by a set of three unique pi-pi interactions.