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CAS 156198-94-6
((2R,5S)-5-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl dihydrogen phosphate
Codes: EMTR-028
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.
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
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: 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
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
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