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CAS 89-78-1
(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol
Codes: TICA-035, LAMI-013, EMTR-032, BEPO-009
Application context (from source-drug indications)
StrokeTicagrelorAcute coronary syndromeTicagrelorMyocardial infarctionTicagrelorPeripheral vascular diseaseTicagrelorHIV infectionDolutegravir/Lamivudine/Tenofovir AlafenamideHIV infectionLamivudine/Tenofovir Disoproxil FumarateChronic hepatitis BLamivudine/Tenofovir Disoproxil FumarateHIV infectionBictegravir/Emtricitabine/Tenofovir Alafenamide FumarateHepatitis BBictegravir/Emtricitabine/Tenofovir Alafenamide FumarateHIV infectionEfavirenz/Lamivudine/Tenofovir Disoproxil FumarateHIV infectionEmtricitabine/Tenofovir Alafenamide FumarateAcquired immunodeficiency syndromeEmtricitabine/Tenofovir Alafenamide FumarateProgressive multifocal leukoencephalopathyEmtricitabine/Tenofovir Alafenamide FumarateHIV infectionEmtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateHepatitis BLamivudineChronic hepatitis BLamivudineHIV infectionLamivudineRett syndromeLamivudineAlzheimer's diseaseLamivudineRetinal detachmentLamivudineHIV infectionEmtricitabineAlzheimer's diseaseEmtricitabineDementiaEmtricitabineMild cognitive impairmentEmtricitabineAllergic rhinitisBepotastine besilateUrticariaBepotastine besilate痒疹Bepotastine besilateAllergic conjunctivitisBepotastine besilatePerennial allergic rhinitisBepotastine besilateInfectious skin diseaseBepotastine besilate
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Ticagrelor | Tier B — Position early | 2029 |
| Dolutegravir/Lamivudine/Tenofovir Alafenamide | Tier C — Watch / trade | - |
| Lamivudine/Tenofovir Disoproxil Fumarate | Tier C — Watch / trade | - |
| Bictegravir/Emtricitabine/Tenofovir Alafenamide Fumarate | Tier B — Position early | - |
| Efavirenz/Lamivudine/Tenofovir Disoproxil Fumarate | Tier C — Watch / trade | - |
| Emtricitabine/Tenofovir Alafenamide Fumarate | Tier B — Position early | - |
| Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil Fumarate | Tier B — Position early | - |
| Lamivudine | Tier C — Watch / trade | - |
| Emtricitabine | Tier C — Watch / trade | - |
| Bepotastine besilate | 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.
(1R,2S)-2-(3,4-difluorophenyl)cyclopropan-1-amine→3,4-difluorobenzaldehyde→malonic acid→(E)-3-(3,4-difluorophenyl)acrylic acid→(E)-3-(3,4-difluorophenyl)acryloyl chloride→(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (E)-3-(3,4-difluorophenyl)acrylate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (1R,2R)-2-(3,4-difluorophenyl)cyclopropane-1-carboxylate→(1R,2R)-2-(3,4-difluorophenyl)cyclopropane-1-carboxylic acid→(1R,2R)-2-(3,4-difluorophenyl)cyclopropane-1-carbonyl azide
4-aminopyrimidin-2(1H)-one→(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→2-oxoacetic acid hydrate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-oxoacetate→1,4-dithiane-2,5-diol→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate
(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate→2-mercaptoacetic acid→2-oxoacetic acid→5-oxo-1,3-oxathiolane-2-carboxylic acid→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-oxo-1,3-oxathiolane-2-carboxylate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate→(2S,5R)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate
4-aminopyrimidin-2(1H)-one→(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→2-oxoacetic acid hydrate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-oxoacetate→1,4-dithiane-2,5-diol→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate
(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate→2-mercaptoacetic acid→2-oxoacetic acid→5-oxo-1,3-oxathiolane-2-carboxylic acid→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-oxo-1,3-oxathiolane-2-carboxylate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate→(2S,5R)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate
1,4-dithiane-2,5-diol→2-oxoacetic acid→5-hydroxy-1,3-oxathiolane-2-carboxylic acid→(2R,5R)-5-acetoxy-1,3-oxathiolane-2-carboxylic acid→(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→(2R,5R)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate→4-amino-5-fluoropyrimidin-2(1H)-one→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate
5-fluoro-N-(trimethylsilyl)-2-((trimethylsilyl)oxy)pyrimidin-4-amine→1,4-dithiane-2,5-diol→2-oxoacetic acid→(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-oxoacetate→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-chloro-1,3-oxathiolane-2-carboxylate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate oxalate→4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one hydrochloride
4-aminopyrimidin-2(1H)-one→(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→2-oxoacetic acid hydrate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-oxoacetate→1,4-dithiane-2,5-diol→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate
(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate→2-mercaptoacetic acid→2-oxoacetic acid→5-oxo-1,3-oxathiolane-2-carboxylic acid→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-oxo-1,3-oxathiolane-2-carboxylate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate→(2S,5R)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate
1,4-dithiane-2,5-diol→2-oxoacetic acid→5-hydroxy-1,3-oxathiolane-2-carboxylic acid→(2R,5R)-5-acetoxy-1,3-oxathiolane-2-carboxylic acid→(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→(2R,5R)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate→4-amino-5-fluoropyrimidin-2(1H)-one→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate
5-fluoro-N-(trimethylsilyl)-2-((trimethylsilyl)oxy)pyrimidin-4-amine→1,4-dithiane-2,5-diol→2-oxoacetic acid→(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-oxoacetate→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-chloro-1,3-oxathiolane-2-carboxylate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate oxalate→4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one hydrochloride
Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateOptimised routesteps: 5total yield: 45 mg
1,4-dithiane-2,5-diol→2-oxoacetic acid→5-hydroxy-1,3-oxathiolane-2-carboxylic acid→(2R,5R)-5-acetoxy-1,3-oxathiolane-2-carboxylic acid→(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→(2R,5R)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate→4-amino-5-fluoropyrimidin-2(1H)-one→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate
Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateOptimised routesteps: 6total yield: 80 g
5-fluoro-N-(trimethylsilyl)-2-((trimethylsilyl)oxy)pyrimidin-4-amine→1,4-dithiane-2,5-diol→2-oxoacetic acid→(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-oxoacetate→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-chloro-1,3-oxathiolane-2-carboxylate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate oxalate→4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one hydrochloride
4-aminopyrimidin-2(1H)-one→(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→2-oxoacetic acid hydrate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-oxoacetate→1,4-dithiane-2,5-diol→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate
(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate→2-mercaptoacetic acid→2-oxoacetic acid→5-oxo-1,3-oxathiolane-2-carboxylic acid→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-oxo-1,3-oxathiolane-2-carboxylate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate→(2S,5R)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate
1,4-dithiane-2,5-diol→2-oxoacetic acid→5-hydroxy-1,3-oxathiolane-2-carboxylic acid→(2R,5R)-5-acetoxy-1,3-oxathiolane-2-carboxylic acid→(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→(2R,5R)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate→4-amino-5-fluoropyrimidin-2(1H)-one→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate
5-fluoro-N-(trimethylsilyl)-2-((trimethylsilyl)oxy)pyrimidin-4-amine→1,4-dithiane-2,5-diol→2-oxoacetic acid→(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-oxoacetate→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-chloro-1,3-oxathiolane-2-carboxylate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate oxalate→4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one hydrochloride
2-((4-chlorophenyl)(piperidin-4-yloxy)methyl)pyridine→(S)-4-(4-((4-chlorophenyl)(pyridin-2-yl)methoxy)piperidin-1-yl)butanoic acid→benzenesulfonic acid→4-chlorobutanoyl chloride→(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-bromobutanoate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-(4-((S)-(4-chlorophenyl)(pyridin-2-yl)methoxy)piperidin-1-yl)butanoate→piperidin-4-ol→1-(4-hydroxypiperidin-1-yl)ethanone→2-(chloro(4-chlorophenyl)methyl)pyridine
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