159005-59-1

Basic information

• Product Name: Carbamic acid, [(1S,2R)-2-hydroxy-3-[(2-methylpropyl)[(4-nitrophenyl)sulfonyl]amino]-1-( phenylmethyl)propyl]-, phenylmethyl ester
• CAS NO: 159005-59-1
• Molecular Formula: C28H33N3O7S
• Molecular Weight: 555.652
• Mol File: 159005-59-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [(1S,2R)-2-hydroxy-3-[(2-methylpropyl)[(4-nitrophenyl)sulfonyl]amino]-1-( phenylmethyl)propyl]-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1S,2R)-2-hydroxy-3-[(2-methylpropyl)[(4-nitrophenyl)sulfonyl]amino]-1-( phenylmethyl)propyl]-, phenylmethyl ester(159005-59-1)
• EPA Substance Registry System: Carbamic acid, [(1S,2R)-2-hydroxy-3-[(2-methylpropyl)[(4-nitrophenyl)sulfonyl]amino]-1-( phenylmethyl)propyl]-, phenylmethyl ester(159005-59-1)

Safety Data

• Hazardous Substances Data: 159005-59-1(Hazardous Substances Data)

Upstream product

• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 143224-62-8 (2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-1-(N-isobutylamino)-4-phenylbutane 

Downstream Products

• 206361-99-1 darunavir 
• 1053738-39-8 (S)-N-{(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-2-methanesulfonylamino-3-(naphthalene-2-sulfinyl)-propionamide 
• 1053640-47-3 (S)-2-Amino-N-{(1S,2R)-1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-3-(naphthalen-2-ylsulfanyl)-propionamide 
• 656236-05-4 N-{(1S,2R)-3-[(2-amino-benzothiazole-6-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxypropyl}-2-(2,6-dimethyl-phenoxy)-acetamide 
• 656236-15-6 {(1S,2R)-3-[(2-amino-benzothiazole-6-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxypropyl}-carbamic acid pyridin-3-ylmethyl ester 
• 656236-11-2 N-{(1S,2R)-3-[(2-amino-benzothiazole-6-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxypropyl}-2-methyl-benzamide 
• 169280-61-9 carbamic acid, 2R-hydroxy-3-[[(2-aminobenzothiazol-6-yl)sulfonyl](2-methylpropyl)amino]-1S-(phenylmethyl)propyl-, phenylmethyl ester 
• 183004-95-7 3-S-(N-t-butyloxyformamido)-2R-hydroxy-1-[(2-aminobenzothiazol-6-sulfonyl)(2-methylpropyl)amino]-4-phenylbutane 
• 183004-96-8 N-[(1S,2R)-3-[(6-benzothiazolylsulfonyl)-(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-carbamic acid-1,1-dimethylethyl ester 
• 183004-94-6 3-S-(N-tert-butyloxyformamido)-[2R-hydroxy-1-[(4-aminophenylsulfonyl)(2-methylpropyl)]amino]-4-phenylbutane 

Relevant articles and documents

The Chiron Approach to (3 R,3 aS,6 aR)-Hexahydrofuro[2,3- b]furan-3-ol, a Key Subunit of HIV-1 Protease Inhibitor Drug, Darunavir

We describe an enantioselective synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol which is a key subunit of darunavir, a widely used HIV-1 protease inhibitor drug for the treatment of HIV/AIDS patients. The synthesis was achieved in optically pure form utilizing commercially available sugar derivatives as the starting material. The key steps involve a highly stereoselective substrate-controlled hydrogenation, a Lewis acid catalyzed anomeric reduction of a 1,2-O-isopropylidene-protected glycofuranoside, and a Baeyer-Villiger oxidation of a tetrahydrofuranyl-2-aldehyde derivative. This optically active ligand alcohol was converted to darunavir efficiently.

New approaches to the industrial synthesis of HIV protease inhibitors

Efficient and industrially applicable synthetic processes for precursors of HIV protease inhibitors (Amprenavir, Fosamprenavir) are described. These involve a novel and economical method for the preparation of a key intermediate, (3S)-hydroxytetrahydrofuran, from L-malic acid. Three new approaches to the assembly of Amprenavir are also discussed. Of these, a synthetic route in which an (S)-tetrahydrofuranyloxy carbonyl is attached to L-phenylalanine appears to be the most promising manufacturing process, in that it offers satisfactory stereoselectivity in fewer steps.

Reduction of peptide character of HIV protease inhibitors that exhibit nanomolar potency against multidrug resistant HIV-1 strains

Novel HIV protease inhibitors containing a hydroxyethylamine dipeptide isostere as a transition state-mimic king structure were synthesized by combining substructures of known HIV protease inhibitors. Among them, TYA5 and TYB5 were proven to be not only p