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CAS 40018-26-6
1,4-dithiane-2,5-diol1,4-Dithiane-2,5-diol
Codes: LAMI-016, EMTR-022, Ticlopidine-006
Application context (from source-drug indications)
HIV 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 FumarateArterial occlusive diseaseTiclopidine Hydrochloride/Ginkgo Biloba Leaf Dried ExtractCerebrovascular diseaseTiclopidine Hydrochloride/Ginkgo Biloba Leaf Dried ExtractEmbolism and thrombosisTiclopidine Hydrochloride/Ginkgo Biloba Leaf Dried ExtractCarotid artery stenosisTiclopidine Hydrochloride/Ginkgo Biloba Leaf Dried ExtractHepatitis BLamivudineChronic hepatitis BLamivudineHIV infectionLamivudineRett syndromeLamivudineAlzheimer's diseaseLamivudineRetinal detachmentLamivudineHIV infectionEmtricitabineAlzheimer's diseaseEmtricitabineDementiaEmtricitabineMild cognitive impairmentEmtricitabineThromboembolismTiclopidine HydrochlorideArterial occlusive diseaseTiclopidine HydrochlorideTransient ischaemic attackTiclopidine HydrochlorideIntracranial vasospasmTiclopidine HydrochlorideCerebrovascular diseaseTiclopidine HydrochlorideSubarachnoid haemorrhageTiclopidine Hydrochloride
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| 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 | - |
| Ticlopidine Hydrochloride/Ginkgo Biloba Leaf Dried Extract | Tier C — Watch / trade | - |
| Lamivudine | Tier C — Watch / trade | - |
| Emtricitabine | Tier C — Watch / trade | - |
| Ticlopidine Hydrochloride | 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.
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
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
N-(5-fluoro-2-((trimethylsilyl)oxy)pyrimidin-4-yl)acetamide→1,4-dithiane-2,5-diol→2-oxoethyl benzoate→(5-acetoxy-1,3-oxathiolan-2-yl)methyl benzoate→(5-(4-acetamido-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate→4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one→(5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl dihydrogen phosphate→((2R,5S)-5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl dihydrogen phosphate
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
N-(5-fluoro-2-((trimethylsilyl)oxy)pyrimidin-4-yl)acetamide→1,4-dithiane-2,5-diol→2-oxoethyl benzoate→(5-acetoxy-1,3-oxathiolan-2-yl)methyl benzoate→(5-(4-acetamido-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate→4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one→(5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl dihydrogen phosphate→((2R,5S)-5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl dihydrogen phosphate
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: 6total yield: 20 mg
N-(5-fluoro-2-((trimethylsilyl)oxy)pyrimidin-4-yl)acetamide→1,4-dithiane-2,5-diol→2-oxoethyl benzoate→(5-acetoxy-1,3-oxathiolan-2-yl)methyl benzoate→(5-(4-acetamido-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate→4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one→(5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl dihydrogen phosphate→((2R,5S)-5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl dihydrogen phosphate
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
3-Oxopentanedioic acid dimethyl diester→1,4-Dithiane-2,5-diol→Methyl 2-(2-methoxy-2-oxoethyl)thiophene-3-carboxylate→2-[3-(Hydroxymethyl)thiophen-2-yl]ethanol→2-(2-Hydroxyethyl)thiophene→2-(2-Bromoethyl)-3-(bromomethyl)thiophene→1-(2-Chlorophenyl)methanamine→5-(2-Chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine→2-(Carboxymethyl)thiophene-3-carboxylic acid→2-[2-(Methoxymethoxy)ethyl]thiophene→6,7-Dihydro-4H-thieno[3,2-c]pyran→2-[2-[(2-Methoxyethoxy)methoxy]ethyl]thiophene
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
N-(5-fluoro-2-((trimethylsilyl)oxy)pyrimidin-4-yl)acetamide→1,4-dithiane-2,5-diol→2-oxoethyl benzoate→(5-acetoxy-1,3-oxathiolan-2-yl)methyl benzoate→(5-(4-acetamido-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate→4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one→(5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl dihydrogen phosphate→((2R,5S)-5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl dihydrogen phosphate
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
3-Oxopentanedioic acid dimethyl diester→1,4-Dithiane-2,5-diol→Methyl 2-(2-methoxy-2-oxoethyl)thiophene-3-carboxylate→2-[3-(Hydroxymethyl)thiophen-2-yl]ethanol→2-(2-Hydroxyethyl)thiophene→2-(2-Bromoethyl)-3-(bromomethyl)thiophene→1-(2-Chlorophenyl)methanamine→5-(2-Chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine→2-(Carboxymethyl)thiophene-3-carboxylic acid→2-[2-(Methoxymethoxy)ethyl]thiophene→6,7-Dihydro-4H-thieno[3,2-c]pyran→2-[2-[(2-Methoxyethoxy)methoxy]ethyl]thiophene
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