143224-62-8

Basic information

• Product Name: Carbamic acid, [(1S,2R)-2-hydroxy-3-[(2-methylpropyl)amino]-1-(phenylmethyl)propyl]-, phenylmethyl ester
• CAS NO: 143224-62-8
• Molecular Formula: C22H30N2O3
• Molecular Weight: 370.492
• Mol File: 143224-62-8.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [(1S,2R)-2-hydroxy-3-[(2-methylpropyl)amino]-1-(phenylmethyl)propyl]-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1S,2R)-2-hydroxy-3-[(2-methylpropyl)amino]-1-(phenylmethyl)propyl]-, phenylmethyl ester(143224-62-8)
• EPA Substance Registry System: Carbamic acid, [(1S,2R)-2-hydroxy-3-[(2-methylpropyl)amino]-1-(phenylmethyl)propyl]-, phenylmethyl ester(143224-62-8)

Safety Data

• Hazardous Substances Data: 143224-62-8(Hazardous Substances Data)

Upstream product

• 78-81-9 isobutylamine 
• 198020-19-8 (2R,2S)-(3S)-1,2-epoxy-3-phenylmethoxycarbonylamino-4-phenylbutane 
• 15196-02-8 (S)-3-[(benzyloxycarbonyl)amino]-1-diazo-4-phenyl-2-butanone 
• 1161-13-3 N-Cbz-L-Phe 
• 128018-43-9 N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2(S)-butanol 
• 26049-94-5 (S)-benzyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate 
• 128018-44-0 N-benzyloxycarbonyl-3(S)-amino-1,2(S)epoxy-4-phenylbutane 

Downstream Products

• 143224-63-9 [2(R),3(S)]-N-[[3-(phenylmethylcarbamoyl)amino-2-hydroxy-4-phenyl]-1-[(2-methylpropyl)]amino-2-(1,1-dimethyl)aminocarbonyl]butane 
• 169280-56-2 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide 
• 181124-41-4 N-[2R-hydroxy-3-[[(2-carbomethoxyamino-benzimidazole-5-yl)sulfonyl](2-methylpropyl)-amino]-1S-(phenylmethyl) propyl]carbamic acid phenylmethyl ester 
• 553645-13-9 C₂₀H₂₇BrN₂O₃S 
• 1245739-25-6 C₃₂H₃₈N₄O₅S 
• 1245739-26-7 C₃₀H₃₄BrN₃O₄S 
• 1245739-28-9 C₃₃H₄₀N₄O₅S 
• 1245739-29-0 C₃₁H₃₆BrN₃O₄S 
• 1245739-31-4 C₃₄H₄₂N₄O₅S 
• 1245739-32-5 C₃₂H₃₈BrN₃O₄S 
• 1245739-33-6 C₃₂H₃₆N₄O₇S 
• 1245739-34-7 C₃₀H₃₂BrN₃O₆S 
• 1245739-36-9 C₃₃H₃₈N₄O₇S 
• 1245739-37-0 C₃₁H₃₄BrN₃O₆S 

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.

Bis-amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors

Selected bis-amino acid hydroxyethylamino sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease. The present invention relates to such retroviral protease inhibitors and, more particularly, relates to selected novel compounds, composition and method for inhibiting retroviral proteases, such as human immunodeficiency virus (HIV) protease, prophylactically preventing retroviral infection or the spread of a retrovirus, and treatment of a retroviral infection.