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Darunavir Ethanolate
Tier B — Position earlyDarunavir Ethanolate
Tibotec
Originator
2006
First approval
-
Expiry (public)
$2.18B ▲
Peak sales
Small molecule
Type
Targets：HIV-1 protease
Brand：Prezista, darunavir
Indications (approved)：HIV infection
Regional status
US
Approved
2006-06-23
EU
Approved
2007-02-11
China
Approved
2008-09-02
Japan
Approved
2007-11-22
Synthetic routes & intermediates5 routes
Originator routes × 1Optimised (non-patent) × 4Process routes × 0
Routes are ordered originator first, then optimised / process (non-patent) routes; each lists steps, overall yield and the intermediate table (code / CAS / name) — ready for supplier sourcing and RFQ. Rendered by this site from structured data; no third-party route graphics used.
OriginatorRoute 1Steps 13 · Total yield 85 mg
DARU-0011191-99-7DARU-002107-19-7DARU-003180902-29-8DARU-004329309-68-4DARU-005809286-93-9DARU-0062089459-22-1DARU-007156928-09-5DARU-00874124-79-1DARU-009253265-97-3DARU-010169280-56-2DARU-011930-22-3DARU-01242238-15-3DARU-013—DARU-014116949-67-8DARU-015136465-89-9DARU-01678-81-9DARU-017206361-96-8DARU-01898-74-8API · Darunavir Ethanolate
| Code | CAS No. | Intermediate |
|---|---|---|
| DARU-001 | 1191-99-7 | 2,3-dihydrofuran |
| DARU-002 | 107-19-7Available | prop-2-yn-1-ol |
| DARU-003 | 180902-29-8 | (2R,3S)-3-iodo-2-(prop-2-yn-1-yloxy)tetrahydrofuran |
| DARU-004 | 329309-68-4 | (3aS,6aR)-3-methylenehexahydrofuro[2,3-b]furan |
| DARU-005 | 809286-93-9 | (3aR,6aR)-tetrahydrofuro[2,3-b]furan-3(2H)-one |
| DARU-006 | 2089459-22-1 | (3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol |
| DARU-007 | 156928-09-5 | (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol |
| DARU-008 | 74124-79-1 | bis(2,5-dioxopyrrolidin-1-yl) carbonate |
| DARU-009 | 253265-97-3 | 2,5-dioxopyrrolidin-1-yl ((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl) carbonate |
| DARU-010 | 169280-56-2 | 4-amino-N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide |
| DARU-011 | 930-22-3 | 2-vinyloxirane |
| DARU-012 | 42238-15-3 | (E)-4-phenylbut-2-en-1-ol |
| DARU-013 | - | ((2R,3R)-3-benzyloxiran-2-yl)methanol |
| DARU-014 | 116949-67-8 | (2S,3S)-3-azido-4-phenylbutane-1,2-diol |
| DARU-015 | 136465-89-9 | (S)-2-((S)-1-azido-2-phenylethyl)oxirane |
| DARU-016 | 78-81-9 | 2-methylpropan-1-amine |
| DARU-017 | 206361-96-8 | (2R,3S)-3-azido-1-(isobutylamino)-4-phenylbutan-2-ol |
| DARU-018 | 98-74-8 | 4-nitrobenzenesulfonyl chloride |
OptimisedRoute 2Steps 5 · Total yield 75 mg
DARU-009253265-97-3DARU-010169280-56-2DARU-01678-81-9DARU-01898-74-8DARU-01998737-29-2DARU-020160232-08-6DARU-021191226-98-9DARU-022183004-94-6API · Darunavir Ethanolate
| Code | CAS No. | Intermediate |
|---|---|---|
| DARU-009 | 253265-97-3 | 2,5-dioxopyrrolidin-1-yl ((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl) carbonate |
| DARU-010 | 169280-56-2 | 4-amino-N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide |
| DARU-016 | 78-81-9 | 2-methylpropan-1-amine |
| DARU-018 | 98-74-8 | 4-nitrobenzenesulfonyl chloride |
| DARU-019 | 98737-29-2 | tert-butyl ((S)-1-((S)-oxiran-2-yl)-2-phenylethyl)carbamate |
| DARU-020 | 160232-08-6 | tert-butyl ((2S,3R)-3-hydroxy-4-(isobutylamino)-1-phenylbutan-2-yl)carbamate |
| DARU-021 | 191226-98-9 | tert-butyl ((2S,3R)-3-hydroxy-4-(N-isobutyl-4-nitrophenylsulfonamido)-1-phenylbutan-2-yl)carbamate |
| DARU-022 | 183004-94-6 | tert-butyl ((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate |
OptimisedRoute 3Steps 6 · Total yield 136.5 g
DARU-007156928-09-5DARU-01678-81-9DARU-023110-63-4DARU-024549509-20-8DARU-0251318642-48-6DARU-0261318642-02-2DARU-027166987-16-2DARU-0281318641-60-9DARU-029664344-42-7DARU-03024939-24-0API · Darunavir Ethanolate
| Code | CAS No. | Intermediate |
|---|---|---|
| DARU-007 | 156928-09-5 | (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol |
| DARU-016 | 78-81-9 | 2-methylpropan-1-amine |
| DARU-023 | 110-63-4 | butane-1,4-diol |
| DARU-024 | 549509-20-8 | (9H-fluoren-9-yl)methyl (4-hydroxybutyl) carbonate |
| DARU-025 | 1318642-48-6 | (9H-fluoren-9-yl)methyl (4-oxobutyl) carbonate |
| DARU-026 | 1318642-02-2 | (9H-fluoren-9-yl)methyl (2-oxoethyl) carbonate |
| DARU-027 | 166987-16-2 | (2S,3S)-3-amino-1-chloro-4-phenylbutan-2-ol hydrochloride |
| DARU-028 | 1318641-60-9 | (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate |
| DARU-029 | 664344-42-7 | (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-3-hydroxy-4-(isobutylamino)-1-phenylbutan-2-yl)carbamate |
| DARU-030 | 24939-24-0 | 4-aminobenzenesulfonyl chloride |
OptimisedRoute 4Steps 11 · Total yield /
DARU-003180902-29-8DARU-007156928-09-5DARU-00874124-79-1DARU-009253265-97-3DARU-010169280-56-2DARU-03160656-87-3DARU-0321826-67-1DARU-03393553-66-3DARU-034108-22-5DARU-035109613-59-4DARU-036814-68-6DARU-037681463-02-5DARU-03872605-53-9DARU-039646-06-0DARU-040681463-03-6DARU-041140156-47-4DARU-042252873-50-0API · Darunavir Ethanolate
| Code | CAS No. | Intermediate |
|---|---|---|
| DARU-003 | 180902-29-8 | (2R,3S)-3-iodo-2-(prop-2-yn-1-yloxy)tetrahydrofuran |
| DARU-007 | 156928-09-5 | (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol |
| DARU-008 | 74124-79-1 | bis(2,5-dioxopyrrolidin-1-yl) carbonate |
| DARU-009 | 253265-97-3 | 2,5-dioxopyrrolidin-1-yl ((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl) carbonate |
| DARU-010 | 169280-56-2 | 4-amino-N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide |
| DARU-031 | 60656-87-3 | 2-(benzyloxy)acetaldehyde |
| DARU-032 | 1826-67-1Available | vinylmagnesium bromide |
| DARU-033 | 93553-66-3 | 1-(benzyloxy)but-3-en-2-ol |
| DARU-034 | 108-22-5 | prop-1-en-2-yl acetate |
| DARU-035 | 109613-59-4 | (S)-1-(benzyloxy)but-3-en-2-ol |
| DARU-036 | 814-68-6Available | acryloyl chloride |
| DARU-037 | 681463-02-5 | (S)-1-(benzyloxy)but-3-en-2-yl acrylate |
| DARU-038 | 72605-53-9 | (S)-5-((benzyloxy)methyl)furan-2(5H)-one |
| DARU-039 | 646-06-0 | 1,3-dioxolane |
| DARU-040 | 681463-03-6 | (4S,5S)-5-((benzyloxy)methyl)-4-(1,3-dioxolan-2-yl)dihydrofuran-2(3H)-one |
| DARU-041 | 140156-47-4 | (4S,5S)-4-(1,3-dioxolan-2-yl)-5-(hydroxymethyl)dihydrofuran-2(3H)-one |
| DARU-042 | 252873-50-0 | (3S,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol |
OptimisedRoute 5Steps 11 · Total yield /
DARU-0436000-00-6DARU-0441423-26-3DARU-045337526-54-2DARU-0461390626-06-8DARU-0471390626-07-9DARU-048—DARU-049—DARU-0501390626-09-1DARU-051—DARU-0521390626-10-4DARU-053—DARU-0541390626-11-5DARU-0551390626-12-6API · Darunavir Ethanolate
| Code | CAS No. | Intermediate |
|---|---|---|
| DARU-043 | 6000-00-6 | methyl (E)-4-bromobut-2-enoate |
| DARU-044 | 1423-26-3 | (3-(trifluoromethyl)phenyl)boronic acid |
| DARU-045 | 337526-54-2 | methyl (E)-4-(3-(trifluoromethyl)phenyl)but-2-enoate |
| DARU-046 | 1390626-06-8 | (E)-4-(3-(trifluoromethyl)phenyl)but-2-en-1-ol |
| DARU-047 | 1390626-07-9 | (E)-1-(4-bromobut-2-en-1-yl)-3-(trifluoromethyl)benzene |
| DARU-048 | - | (2S,3R)-1-bromo-4-(3-(trifluoromethyl)phenyl)butane-2,3-diol |
| DARU-049 | - | (R)-1-((R)-oxiran-2-yl)-2-(3-(trifluoromethyl)phenyl)ethan-1-ol |
| DARU-050 | 1390626-09-1 | (2R,3R)-1-(isobutylamino)-4-(3-(trifluoromethyl)phenyl)butane-2,3-diol |
| DARU-051 | - | tert-butyl ((2R,3R)-2,3-dihydroxy-4-(3-(trifluoromethyl)phenyl)butyl)(isobutyl)carbamate |
| DARU-052 | 1390626-10-4 | (R)-5-((R)-1-hydroxy-2-(3-(trifluoromethyl)phenyl)ethyl)-3-isobutyloxazolidin-2-one |
| DARU-053 | - | (R)-1-((R)-3-isobutyl-2-oxooxazolidin-5-yl)-2-(3-(trifluoromethyl)phenyl)ethyl methanesulfonate |
| DARU-054 | 1390626-11-5 | (R)-5-((S)-1-azido-2-(3-(trifluoromethyl)phenyl)ethyl)-3-isobutyloxazolidin-2-one |
| DARU-055 | 1390626-12-6 | (2R,3S)-3-azido-1-(isobutylamino)-4-(3-(trifluoromethyl)phenyl)butan-2-ol |
Frequently asked questions
What are the approved indications of Darunavir Ethanolate?
Approved indications include: HIV infection.
When does the Darunavir Ethanolate patent expire?
No public expiry year is available for Darunavir Ethanolate yet; this page updates once verified.
How many synthesis routes are recorded for Darunavir Ethanolate?
5 synthesis routes are recorded; the shortest is 5 steps with 75 mg total yield. Intermediates in each route carry codes and CAS numbers.
Where can I buy Darunavir Ethanolate intermediates?
3 intermediate CAS of Darunavir Ethanolate are available through the Unibest supply network — see the route tables on this page and request a quote per CAS.
How do I get a quote for Darunavir Ethanolate intermediates?
Open the CAS profile of the target intermediate from this page, or submit an RFQ directly — the CAS enters the matching flow automatically and the supply network responds with quotes.
Source: cross-verified data (structured fields only) · 2026-09-29