82933-48-0

Upstream product

• 7669-54-7 2-nitrobenzenesulfenyl chloride 
• 137527-27-6 (2S,3R)-3-Hydroxy-2-(2-nitro-phenylsulfanylamino)-butyric acid ethyl ester 
• 937-32-6 4-nitrobenzenesulfenyl chloride 
• 7685-70-3 N-<(o-nitrophenyl)sulfenyl>-L-threonine 
• 82933-45-7 (2S,3R)-N-Benzyloxy-3-hydroxy-2-(2-nitro-phenylsulfanylamino)-butyramide 
• 82933-47-9 Methanesulfonic acid (1R,2S)-2-benzyloxycarbamoyl-1-methyl-2-(2-nitro-phenylsulfanylamino)-ethyl ester 

Downstream Products

• 1155-00-6 bis(2-nitrophenyl)disulfide 
• 54848-83-8 4-methylphenyl 2-nitrophenyl disulfide 
• 131131-06-1 (3S,4R)-2-methyl-4-oxo-3-oxetanylammonium toluene-4-sulfonate 
• 83112-05-4 (3S,4R)-3-(acetylamino)-4-methyl-2-oxetanone 
• 137527-31-2 Acetic acid 2-acetoxy-6-((2R,3S)-2-methyl-4-oxo-oxetan-3-ylcarbamoyl)-phenyl ester 
• 131131-07-2 (3S,4R)-3-(benzoylamino)-4-methyl-2-oxetanone 
• 82933-47-9 Methanesulfonic acid (1R,2S)-2-benzyloxycarbamoyl-1-methyl-2-(2-nitro-phenylsulfanylamino)-ethyl ester 
• 82933-46-8 (3S-trans)-4-Methyl-3-[[(2-nitrophenyl)thio]amino]-1-(phenylmethoxy)-2-azetidinone 
• 131232-75-2 (3S,4S)-3-amino-4-methyl-2-oxetanone p-toluenesulfonate salt 
• 82933-45-7 (2S,3R)-N-Benzyloxy-3-hydroxy-2-(2-nitro-phenylsulfanylamino)-butyramide 

Relevant academic research and scientific papers

A Novel Transacylation Method for the Synthesis of α-N-Acyl-β-lactones; Application to (+/-)-Diacetylobaflorin and (+)-SQ 26,517

Stereoselective synthesis of (+/-)-diacetylobafluorin and (+)-SQ 26,517 has been accomplished via transacylation of α-N-(2-nitrophenyl)sulphenyl-β-lactones with 2-acetylmercaptobenzothiazoles.

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.