105311-53-3

Basic information

• Product Name: 1H-Indole-1-carboxylic acid, 3-[1-[(methylsulfonyl)oxy]ethyl]-, phenylmethyl ester
• CAS NO: 105311-53-3
• Molecular Formula: C19H19NO5S
• Molecular Weight: 373.43
• Mol File: 105311-53-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1H-Indole-1-carboxylic acid, 3-[1-[(methylsulfonyl)oxy]ethyl]-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-1-carboxylic acid, 3-[1-[(methylsulfonyl)oxy]ethyl]-, phenylmethyl ester(105311-53-3)
• EPA Substance Registry System: 1H-Indole-1-carboxylic acid, 3-[1-[(methylsulfonyl)oxy]ethyl]-, phenylmethyl ester(105311-53-3)

Safety Data

• Hazardous Substances Data: 105311-53-3(Hazardous Substances Data)

Upstream product

• 103871-32-5 benzyl 3-acetyl-1H-indole-1-carboxylate 
• 501-53-1 benzyl chloroformate 
• 124-63-0 methanesulfonyl chloride 
• 103871-31-4 (+)-1-(N-carbobenzoxyindol-3-yl)ethanol 

Relevant articles and documents

New Total Synthesis of (+/-)-Indolmycin

A convergent total synthesis of the antibiotic (+/-)-indolmycin (1) is presented.N-Carbobenzoxy-3-(1-chloroethyl)indole (12) is prepared in three steps from indole-3-carboxaldehyde (9).Alkylation of the lithium anion of 2-(dimethylamino)-4(5H)-oxazolone (4) with chloride (12) provides a mixture of the (+/-)-2-dimethylamino derivative of indolmycin (13) and its diastereomer (14) in a ratio of 2.2:1.Amine exchange is effected by treatment of 13 with methylamine, affording (+/-)-1 in five steps from commercially available 9.Efforts to extend this technology toward an asymmetric synthesis of (-)-1 are described.