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CAS 160232-08-6
tert-butyl ((2S,3R)-3-hydroxy-4-(isobutylamino)-1-phenylbutan-2-yl)carbamate
Codes: DARU-020, FOSAC-001
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.
2,5-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-methylpropan-1-amine→4-nitrobenzenesulfonyl chloride→tert-butyl ((S)-1-((S)-oxiran-2-yl)-2-phenylethyl)carbamate→tert-butyl ((2S,3R)-3-hydroxy-4-(isobutylamino)-1-phenylbutan-2-yl)carbamate→tert-butyl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-nitrophenylsulfonamido)-1-phenylbutan-2-yl)carbamate→tert-butyl ((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate
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-methylpropan-1-amine→4-nitrobenzenesulfonyl chloride→tert-butyl ((S)-1-((S)-oxiran-2-yl)-2-phenylethyl)carbamate→tert-butyl ((2S,3R)-3-hydroxy-4-(isobutylamino)-1-phenylbutan-2-yl)carbamate→tert-butyl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-nitrophenylsulfonamido)-1-phenylbutan-2-yl)carbamate→tert-butyl ((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate
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-methylpropan-1-amine→4-nitrobenzenesulfonyl chloride→tert-butyl ((S)-1-((S)-oxiran-2-yl)-2-phenylethyl)carbamate→tert-butyl ((2S,3R)-3-hydroxy-4-(isobutylamino)-1-phenylbutan-2-yl)carbamate→tert-butyl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-nitrophenylsulfonamido)-1-phenylbutan-2-yl)carbamate→tert-butyl ((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate
tert-butyl ((2S,3R)-3-hydroxy-4-(isobutylamino)-1-phenylbutan-2-yl)carbamate→benzyl ((2R,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4-phenylbutyl)(isobutyl)carbamate→benzyl ((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)(isobutyl)carbamate hydrochloride→(S)-2,5-dioxopyrrolidin-1-yl (tetrahydrofuran-3-yl) carbonate→benzyl ((2R,3S)-2-hydroxy-4-phenyl-3-(((((S)-tetrahydrofuran-3-yl)oxy)carbonyl)amino)butyl)(isobutyl)carbamate→(S)-tetrahydrofuran-3-yl ((2S,3R)-3-hydroxy-4-(isobutylamino)-1-phenylbutan-2-yl)carbamate→4-nitrobenzenesulfonyl chloride→(S)-tetrahydrofuran-3-yl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-nitrophenylsulfonamido)-1-phenylbutan-2-yl)carbamate
tert-butyl ((2S,3R)-3-hydroxy-4-(isobutylamino)-1-phenylbutan-2-yl)carbamate→4-nitrobenzenesulfonyl chloride→(S)-tetrahydrofuran-3-yl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-nitrophenylsulfonamido)-1-phenylbutan-2-yl)carbamate→L-phenylalanine→(S)-2-(dibenzylamino)-3-phenylpropanal→(2S,3S)-1-chloro-3-(dibenzylamino)-4-phenylbutan-2-ol hydrochloride→(2S,3S)-3-amino-1-chloro-4-phenylbutan-2-ol hydrochloride→tert-butyl ((S)-1-((S)-oxiran-2-yl)-2-phenylethyl)carbamate→N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitrobenzenesulfonamide hydrochloride→(S)-tetrahydrofuran-3-yl 1H-imidazole-1-carboxylate→(S)-tetrahydrofuran-3-yl ((2S,3R)-4-((N-isobutyl-4-nitrophenyl)sulfonamido)-1-phenyl-3-(phosphonooxy)butan-2-yl)carbamate→(S)-tetrahydrofuran-3-yl ((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-1-phenyl-3-(phosphonooxy)butan-2-yl)carbamate
tert-butyl ((2S,3R)-3-hydroxy-4-(isobutylamino)-1-phenylbutan-2-yl)carbamate→tert-butyl ((S)-1-((S)-oxiran-2-yl)-2-phenylethyl)carbamate→(S)-tetrahydrofuran-3-yl 1H-imidazole-1-carboxylate→(S)-tetrahydrofuran-3-yl ((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-1-phenyl-3-(phosphonooxy)butan-2-yl)carbamate→4-(1,3-dioxoisoindolin-2-yl)benzenesulfonyl chloride→N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-4-(1,3-dioxoisoindolin-2-yl)-N-isobutylbenzenesulfonamide hydrochloride→(S)-tetrahydrofuran-3-yl ((2S,3R)-4-((4-(1,3-dioxoisoindolin-2-yl)-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate→(S)-tetrahydrofuran-3-yl ((2S,3R)-4-((4-(1,3-dioxoisoindolin-2-yl)-N-isobutylphenyl)sulfonamido)-1-phenyl-3-(phosphonooxy)butan-2-yl)carbamate
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