147977-21-7

Basic information

• Product Name: (2R,3R)-1,1-dioxido-2-(propan-2-yl)tetrahydrothiophen-3-yl {(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-3-hydroxy-1-phenylbutan-2-yl}carbamate
• Synonyms: 489;L735;L-735;L 735;L-735,489;Aids005134;Aids-005134;Carbamic acid, [(1S,2R)-3-[(3S,4as,8as)-3-[[(1,1-dimethylethyl)amino]carbonyl]octahydro-2(1H)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-, (2S,3S)-tetrahydro-2-(1-methylethyl)-1,1-dioxido-3-thienyl ester
• CAS NO: 147977-21-7
• Molecular Formula: C₃₂H₅₁N₃O₆S
• Molecular Weight: 605.8288
• Mol File: 147977-21-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 815.4°C at 760 mmHg
• Flash Point: 446.9°C
• Density: 1.21g/cm³
• Vapor Pressure: 4.1E-28mmHg at 25°C
• Refractive Index: 1.572
• CAS DataBase Reference: (2R,3R)-1,1-dioxido-2-(propan-2-yl)tetrahydrothiophen-3-yl {(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-3-hydroxy-1-phenylbutan-2-yl}carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-1,1-dioxido-2-(propan-2-yl)tetrahydrothiophen-3-yl {(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-3-hydroxy-1-phenylbutan-2-yl}carbamate(147977-21-7)
• EPA Substance Registry System: (2R,3R)-1,1-dioxido-2-(propan-2-yl)tetrahydrothiophen-3-yl {(2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-3-hydroxy-1-phenylbutan-2-yl}carbamate(147977-21-7)

Safety Data

• Hazardous Substances Data: 147977-21-7(Hazardous Substances Data)

Upstream product

• 147949-28-8 [(1S,2R)-1-Benzyl-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-propyl]-carbamic acid (2R,3R)-2-isopropyl-tetrahydro-thiophen-3-yl ester 
• 153325-09-8 2(S)-(1-methylethyl)-3(R)-hydroxytetrahydrothiophene 
• 136465-90-2 N-tert-butyl-2-<2(R)-hydroxy-4-phenyl-3(S)-azidobutyl>decahydro(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 136522-17-3 cis-N-butyldecahydro-2-<2(R)-hydroxy-4-phenyl-3(S)-aminobutyl>-(4aS,8aS)-isoquinoline-3(S)-carboxamide 
• 128019-40-9 (3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide 
• 136465-89-9 (2S)-2-[1'(S)-1-azido-2-phenylethyl]oxirane 
• 147949-27-7 Carbonic acid (2R,3R)-2-isopropyl-tetrahydro-thiophen-3-yl ester pyridin-2-yl ester 
• 147949-26-6 2(R)-(1-methylethyl)-3(R)-hydroxytetrahydrothioiphene 
• 147949-23-3 3(R)-<(methoxymethyl)oxy>-4(S)-(1-methylethyl)-1,4-bis<(methylsulfonyl)oxy>butane 
• 147949-37-9 (4R,5S)-5-Isopropyl-4-methoxymethoxy-dihydro-furan-2-one 
• 147977-16-0 4(S)-(1-methylethyl)-3(R)-hydroxy-γ-butyrolactone 
• 147949-24-4 3(R)-<(methoxymethyl)oxy>-2(R)-(1-methylethyl)tetrahydrothiophene 
• 147949-38-0 (3R,4S)-3-Methoxymethoxy-5-methyl-hexane-1,4-diol 

Relevant articles and documents

The Development of Cyclic Sulfolanes as Novel and High-Affinity P2 Ligands for HIV-1 Protease Inhibitors

Design and synthesis of a novel series of protease inhibitors incorporating conformationally constrained cyclic ligands for the S2-substrate binding site of HIV-1 protease is described. We recently reported urethanes of 3-tetrahydrofuranyl as P2 ligands for HIV-1 protease inhibitors. Subsequently, we have found that the urethane of 3(S)-hydroxysulfolane further increased the in vitro potency of these inhibitors. Furthermore, introduction of a small 2-alkyl group cis to the 3-hydroxyl group of either heterocyclic system further enhanced enzyme affinity. The cis-2-isopropyl group thus far offered optimum enhancement of the inhibitory properties. This led to the discovery of inhibitor 43 (IC50 3.5 nM, CIC95 50+/-14 nM) of comparable in vitro antiviral potency to the current clinical candidate 1 (Ro 31-8959) but of reduced molecular weight due to the exclusion of the P3 quinoline ligand. Also, it has been demonstrated that the octahydropyrindene derivative 34 is an effective replacement of the P1' decahydroisoquinoline derivative.