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CAS 147027-43-8
(2R,5R)-5-acetoxy-1,3-oxathiolane-2-carboxylic acid
Codes: EMTR-031
Application context (from source-drug indications)
HIV infectionBictegravir/Emtricitabine/Tenofovir Alafenamide FumarateHepatitis BBictegravir/Emtricitabine/Tenofovir Alafenamide FumarateHIV infectionEmtricitabine/Tenofovir Alafenamide FumarateAcquired immunodeficiency syndromeEmtricitabine/Tenofovir Alafenamide FumarateProgressive multifocal leukoencephalopathyEmtricitabine/Tenofovir Alafenamide FumarateHIV infectionEmtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateHIV infectionEmtricitabineAlzheimer's diseaseEmtricitabineDementiaEmtricitabineMild cognitive impairmentEmtricitabine
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Bictegravir/Emtricitabine/Tenofovir Alafenamide Fumarate | Tier B — Position early | - |
| Emtricitabine/Tenofovir Alafenamide Fumarate | Tier B — Position early | - |
| Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil Fumarate | Tier B — Position early | - |
| Emtricitabine | 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.
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
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: 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
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
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