599173-45-2

Basic information

• Product Name: Carbonic acid, (1R,2S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-[[(2-methylpropyl)[(4- nitrophenyl)sulfonyl]amino]methyl]-3-phenylpropyl methyl ester
• CAS NO: 599173-45-2
• Molecular Formula: C27H37N3O9S
• Molecular Weight: 579.671
• Mol File: 599173-45-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Carbonic acid, (1R,2S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-[[(2-methylpropyl)[(4- nitrophenyl)sulfonyl]amino]methyl]-3-phenylpropyl methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbonic acid, (1R,2S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-[[(2-methylpropyl)[(4- nitrophenyl)sulfonyl]amino]methyl]-3-phenylpropyl methyl ester(599173-45-2)
• EPA Substance Registry System: Carbonic acid, (1R,2S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-[[(2-methylpropyl)[(4- nitrophenyl)sulfonyl]amino]methyl]-3-phenylpropyl methyl ester(599173-45-2)

Safety Data

• Hazardous Substances Data: 599173-45-2(Hazardous Substances Data)

Upstream product

• 79-22-1 methyl chloroformate 
• 191226-98-9 [(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester 

Relevant articles and documents

Novel prodrug approach to amprenavir-based HIV-1 protease inhibitors via O→N acyloxy migration of P1 moiety

We have developed a new approach to prodrugs, which utilizes a pH-induced intramolecular O→N migration of an acyloxy group in carbonate moiety to a free amino moiety at neutral pH. This method is exemplified by facile rearrangement of highly water-soluble prodrug 3 to carbamate 4, a close analogue of HIV-1 protease inhibitor Amprenavir. The O→N acyloxy migration is unprecedented in the context of prodrugs and it enables a high atom economy due to recycling of the 'pro' moiety.