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CAS 206361-96-8
(2R,3S)-3-azido-1-(isobutylamino)-4-phenylbutan-2-ol
Codes: DARU-017, FOSAC-029
Application context (from source-drug indications)
HIV infectionDarunavir Ethanolate/RitonavirHIV infectionDarunavir Ethanolate/CobicistatHIV infectionDarunavir EthanolateHIV infectionFosamprenavir Calcium
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Darunavir Ethanolate/Ritonavir | Tier C — Watch / trade | - |
| Darunavir Ethanolate/Cobicistat | Tier C — Watch / trade | - |
| Darunavir Ethanolate | Tier B — Position early | - |
| Fosamprenavir Calcium | Tier C — Watch / trade | - |
Position in synthesis routes (up/downstream chain)
Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.
2,3-dihydrofuran→prop-2-yn-1-ol→(2R,3S)-3-iodo-2-(prop-2-yn-1-yloxy)tetrahydrofuran→(3aS,6aR)-3-methylenehexahydrofuro[2,3-b]furan→(3aR,6aR)-tetrahydrofuro[2,3-b]furan-3(2H)-one→(3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol→(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol→bis(2,5-dioxopyrrolidin-1-yl) carbonate→2,5-dioxopyrrolidin-1-yl ((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl) carbonate→4-amino-N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide→2-vinyloxirane→(E)-4-phenylbut-2-en-1-ol→((2R,3R)-3-benzyloxiran-2-yl)methanol→(2S,3S)-3-azido-4-phenylbutane-1,2-diol→(S)-2-((S)-1-azido-2-phenylethyl)oxirane→2-methylpropan-1-amine→(2R,3S)-3-azido-1-(isobutylamino)-4-phenylbutan-2-ol→4-nitrobenzenesulfonyl chloride
2,3-dihydrofuran→prop-2-yn-1-ol→(2R,3S)-3-iodo-2-(prop-2-yn-1-yloxy)tetrahydrofuran→(3aS,6aR)-3-methylenehexahydrofuro[2,3-b]furan→(3aR,6aR)-tetrahydrofuro[2,3-b]furan-3(2H)-one→(3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol→(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol→bis(2,5-dioxopyrrolidin-1-yl) carbonate→2,5-dioxopyrrolidin-1-yl ((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl) carbonate→4-amino-N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide→2-vinyloxirane→(E)-4-phenylbut-2-en-1-ol→((2R,3R)-3-benzyloxiran-2-yl)methanol→(2S,3S)-3-azido-4-phenylbutane-1,2-diol→(S)-2-((S)-1-azido-2-phenylethyl)oxirane→2-methylpropan-1-amine→(2R,3S)-3-azido-1-(isobutylamino)-4-phenylbutan-2-ol→4-nitrobenzenesulfonyl chloride
2,3-dihydrofuran→prop-2-yn-1-ol→(2R,3S)-3-iodo-2-(prop-2-yn-1-yloxy)tetrahydrofuran→(3aS,6aR)-3-methylenehexahydrofuro[2,3-b]furan→(3aR,6aR)-tetrahydrofuro[2,3-b]furan-3(2H)-one→(3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol→(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol→bis(2,5-dioxopyrrolidin-1-yl) carbonate→2,5-dioxopyrrolidin-1-yl ((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl) carbonate→4-amino-N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide→2-vinyloxirane→(E)-4-phenylbut-2-en-1-ol→((2R,3R)-3-benzyloxiran-2-yl)methanol→(2S,3S)-3-azido-4-phenylbutane-1,2-diol→(S)-2-((S)-1-azido-2-phenylethyl)oxirane→2-methylpropan-1-amine→(2R,3S)-3-azido-1-(isobutylamino)-4-phenylbutan-2-ol→4-nitrobenzenesulfonyl chloride
4-nitrobenzenesulfonyl chloride→(S)-tetrahydrofuran-3-yl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-nitrophenylsulfonamido)-1-phenylbutan-2-yl)carbamate→(E)-4-phenylbut-2-en-1-ol→(3-benzyloxiran-2-yl)methanol→3-azido-4-phenylbutane-1,2-diol→2-(1-azido-2-phenylethyl)oxirane→Cobalt, [[2,2'-[(1S,2S)-1,2-cyclohexanediylbis[(nitrilo-kN)methylidyne]]bis[4,6-bis(1,1-dimethylethyl)phenolato-kO]](2-)]-, (SP-4-2)-→(S)-2-((S)-1-azido-2-phenylethyl)oxirane→(2R,3S)-3-azido-1-(isobutylamino)-4-phenylbutan-2-ol→N-((2R,3S)-3-azido-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitrobenzenesulfonamide→(S)-tetrahydrofuran-3-yl 2,5-dioxopyrrolidine-1-carboxylate→(S)-tetrahydrofuran-3-yl ((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate
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