54848-83-8

Upstream product

• 7669-54-7 2-nitrobenzenesulfenyl chloride 
• 106-45-6 para-thiocresol 
• 2769-30-4 2-nitrophenyl thiocyanate 
• 22024-99-3 2-nitrobenzenesulfenyl bromide 
• 82933-48-0 (3S,4R)-3-<<(o-nitrophenyl)sulfenyl>amino>-4-methyl-2-oxetanone 
• 104-15-4 toluene-4-sulfonic acid 
• 29572-51-8 2-nitrobenzenesulfenyl thiocyanate 
• 24696-54-6 tri-n-butyltin(4-CH₃-C₆H₄S) 
• 54848-92-9 {2-(p-tolylthio)ethyl}triphenyltin 
• 20804-34-6 N-(p-Toluolsulfonyl)-N,N'-bis-(benzolsulfonyl)-p-toluolsulfinamidin 
• 22755-25-5 o-nitrobenzenethiol sodium salt 

Downstream Products

• 29489-33-6 bis-benzenesulfonyl-p-tolylsulfanyl-methane 

Relevant academic research and scientific papers

Imination of sulfur-containing compounds: XXXV. New preparation method and oxidative benzenesulfonylimination of unsymmetrical disulfides

A new preparative method of synthesis was developed for unsymmetrical and symmetrical disulfides. This method involves sulfenylation of sodium thiolates with N-arenesulfenyl-N,N′-bis(arenesulfonyl)sulfinamidines. Imination of unsymmetrical disulfides with sodium chloroamides of sulfonic acids occurs at the more nucleophilic sulfur atom, affording N,N′ -bis(arenesulfonyl)sulfinamidines and symmetrical disulfides.

Synthesis and Acylation of Salts of L-Threonine β-Lactone: A Route to β-Lactone Antibiotics

The synthesis and N-acylation of β-lactones derived from L-threonine and L-allo-threonine were investigated.Treatment of N--L-allo-threonine (7b) with 4-bromobenzenesulfonyl chloride in pyridine at -43 to 0 deg C gives the corresponding β-lactones 8a and 8b, respectively, in 45-56 percent yields.These can be deprotected with thiophenol or p-thiocresol in the presence of p-toluenesulfonic acid to produce optically pure salts of L-threonine β-lactone (9a) and its allo isomer 9b (65-92percent).Compound 9a is readily acylated by reagents such as acid chlorides (e.g., acetyl, benzoyl) and mixed anhydrides to afford N-acyl β-substituted β-lactones such as 10 (antibiotic SQ 26,517), 14, 15, and 16 in good yield (84-92percent).Reaction of β-lactones 8a, 8b, and 9a with HBr in acetic acid results in nucleophilic ring opening by bromide at the β-position to give pure isomers of 2-amino-3-bromobutanoic acid.