163013-14-7

Basic information

• Product Name: (2R,3R)-(-)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-(1-pentadecenyl)aziridine
• Synonyms: (2R,3R)-(-)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-(1-pentadecenyl)aziridine
• CAS NO: 163013-14-7
• Molecular Weight: 447.682
• Mol File: 163013-14-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2R,3R)-(-)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-(1-pentadecenyl)aziridine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-(-)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-(1-pentadecenyl)aziridine(163013-14-7)
• EPA Substance Registry System: (2R,3R)-(-)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-(1-pentadecenyl)aziridine(163013-14-7)

Safety Data

• Hazardous Substances Data: 163013-14-7(Hazardous Substances Data)

Upstream product

• 1517-82-4 (1S,2R,5S)-2-isopropyl-5-methylcyclohexyl (R)-4-methylbenzenesulfinate 
• 3163-37-9 (E)-hexadec-2-enal 
• 96-32-2 bromoacetic acid methyl ester 
• 163013-12-5 (R)-(-)-N-(E-2-hexadecenylydene)-p-toluenesulfinimide 

Downstream Products

• 113507-74-7 (R)-(-)-2-carbomethoxy-3-(1-pentadecenyl)-2H-azirine 
• 934-72-5 Methyl p-tolyl sulfoxide 

Relevant articles and documents

Asymmetric Synthesis of 2H-Azirine 2-Carboxylate Esters

2H-Azirine 2-carboxylate esters (5), the smallest unsaturated nitrogen heterocycle, are readily prepared in enantiomerically pure form via the base-induced elimination of sulfenic acid (RSOH) from nonracemic N-sulfinylaziridine 2-carboxylate esters (4). Optimum yields were obtained when the aziridine was treated with TMSCl at -95 °C followed by LDA, which was attributed to the improved leaving group ability of an silicon-oxonium species. By using this new methodology the first asymmetric syntheses of the marine cytotoxic antibiotics (R)-(-)- and (S)-(+)-dysidazirine (2) were accomplished.