229495-94-7

Upstream product

• 5070-13-3 bis-(p-nitrophenyl) carbonate 
• 191226-98-9 [(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester 

Downstream Products

• 229495-71-0 Carbonic acid (1R,2S)-2-tert-butoxycarbonylamino-1-{[isobutyl-(4-nitro-benzenesulfonyl)-amino]-methyl}-3-phenyl-propyl ester (S)-(tetrahydro-furan-3-yl) ester 

Relevant academic research and scientific papers

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.