94600-72-3

Upstream product

• 49591-20-0 N-(tert-butyl)benzenesulfinimidoyl chloride 
• 31600-54-1 8-(benzyloxy)octan-1-ol 
• 4972-29-6 benzenesulphinyl chloride 
• 75-64-9 tert-butylamine 
• 100-51-6 benzyl alcohol 
• 98-09-9 benzenesulfonyl chloride 
• 934-87-2 S-phenyl thioacetate 
• 108-98-5 thiophenol 
• 882-33-7 diphenyldisulfane 
• 19117-31-8 N-(phenylthio)-N-(tert-butyl)amine 
• 873-55-2 sodium benzenesulfonate 

Downstream Products

• 13165-80-5 o-(hydroxysulfinyl)benzoic acid 
• 1520120-25-5 3-{[(tert-butylamino)oxophenyl-1λ⁶-sulfanylidene]amino}propanoic acid 
• 1520119-97-4 ethyl 3-{[(tert-butylamino)oxophenyl-1λ⁶-sulfanylidene]amino}propanoate 

Relevant academic research and scientific papers

Boronic acid derivatives

The present invention relates to boronic acid derivatives; the present invention provides compounds of formula (I) or pharmaceutically acceptable salts, solvates, polymorphs or isomers thereof, pharmaceutical compositions comprising these compounds, and u

A study of the reactivity of S(VI)-F containing warheads with nucleophilic amino-acid side chains under physiological conditions

Sulfonyl fluorides (SFs) have recently emerged as a promising warhead for the targeted covalent modification of proteins. Despite numerous examples of the successful deployment of SFs as covalent probe compounds, a detailed exploration of the factors influencing the stability and reactivity of SFs has not yet appeared. In this work we present an extensive study on the influence of steric and electronic factors on the reactivity and stability of the SF and related SVI-F groups. While SFs react rapidly with N-acetylcysteine, the resulting adducts were found to be unstable, rendering SFs inappropriate for the durable covalent inhibition of cysteine residues. In contrast, SFs afforded stable adducts with both N-acetyltyrosine and N-acetyllysine; furthermore, we show that the reactivity of arylsulfonyl fluorides towards these nucleophilic amino acids can be predictably modulated by adjusting the electronic properties of the warhead. These trends were largely conserved when the covalent reaction occurred within a protein binding pocket. We have also obtained a crystal structure depicting covalent modification of the catalytic lysine of a tyrosine kinase (FGFR1) by the ATP analog 5′-O-3-((fluorosulfonyl)benzoyl)adenosine (m-FSBA). Highly reactive warheads were demonstrated to be unstable with respect to hydrolysis in buffered aqueous solutions, indicating that warhead reactivity must be carefully tuned to provide optimal rates of protein modification. Our results demonstrate that the reactivity of SFs complements that of more commonly studied acrylamides, and we hope that this work spurs the rational design of novel SF-containing covalent probe compounds and inhibitors, particularly in cases where a suitably positioned cysteine residue is not present.

Copper-Catalyzed Oxidative Synthesis of Sulfinamides Using Thiols or Disulfides with Amines

Copper-catalyzed coupling of thiols with amines was used to synthesize numerous sulfinamides in excellent yields. Sulfenamides or sulfonamides were also formed as reaction byproducts albeit in trace quantities. The procedure is carried out as a one step a

Synthesis of six-membered cyclic sulfonimidamides

A general synthetic route to six-membered cyclic N-aryl- and N-alkyl-substituted sulfonimidamides via an intramolecular ring closure of suitably functionalised acyclic sulfonimidamides is described. The structure of this new ring system was confirmed by v

Fast and efficient synthesis of sulfinamides by the oxidation of sulfenamides using potassium fluoride and m-chloroperoxybenzoic acid

A procedure for the synthesis of N-alkyl-, N-cycloalkyl-, N,N-dialkyl-, and N-arylarenesulfinamides from the corresponding sulfenamides using KF/m-chloroperoxybenzoic acid (CPBA) in CH3CN-H2O is described. High efficiency (fast react

Copper-catalyzed formation of sulfur-nitrogen bonds by dehydrocoupling of thiols with amines

Copper-catalyzed formation of sulfur-nitrogen bonds can be performed by a dehydrocoupling of aryl thiols with amines. Sulfenamides or sulfonamides can be produced by the use of a copper catalyst in air or under oxygen atmosphere. Furthermore, a reaction involving the combination of a palladium catalyst and a copper catalyst selectively afforded sulfinamides.

Expedient synthesis of sulfinamides from sulfonyl chlorides

Sulfinamides were synthesized from sulfonyl chlorides using a procedure involving in situ reduction of sulfonyl chlorides. The reaction is broad in scope and easy to perform.

A new method for oxidation of various alcohols to the corresponding carbonyl compounds by using n-t-butylbenzenesulfinimidoyl chloride

Various primary and secondary alcohols were smoothly oxidized to the corresponding aldehydes and ketones by using a new oxidizing agent, N-t-butylbenzenesulfinimidoyl chloride (4a), in the coexistence of DBU or zinc oxide. The present oxidation proceeded under mild conditions via five-membered intramolecular proton-transfer of an alkyl arenesulfinimidate intermediate.