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CAS 64904-47-8

2-oxoethyl benzoate

Codes: LAMI-002, EMTR-023, PLAZ-015

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 FumarateHepatitis BLamivudineChronic hepatitis BLamivudineHIV infectionLamivudineRett syndromeLamivudineAlzheimer's diseaseLamivudineRetinal detachmentLamivudineHIV infectionEmtricitabineAlzheimer's diseaseEmtricitabineDementiaEmtricitabineMild cognitive impairmentEmtricitabineBacterial infectionPlazomicin sulfateHospital-acquired pneumoniaPlazomicin sulfateUrinary tract infectionPlazomicin sulfatePyelonephritisPlazomicin sulfateEnd-stage renal diseasePlazomicin sulfate肠杆菌科感染Plazomicin sulfate

Source drugs (routes using this intermediate)

DrugTierExpiry
Dolutegravir/Lamivudine/Tenofovir AlafenamideTier C — Watch / trade-
Lamivudine/Tenofovir Disoproxil FumarateTier C — Watch / trade-
Bictegravir/Emtricitabine/Tenofovir Alafenamide FumarateTier B — Position early-
Efavirenz/Lamivudine/Tenofovir Disoproxil FumarateTier C — Watch / trade-
Emtricitabine/Tenofovir Alafenamide FumarateTier B — Position early-
Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateTier B — Position early-
LamivudineTier C — Watch / trade-
EmtricitabineTier C — Watch / trade-
Plazomicin sulfateTier 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.

Dolutegravir/Lamivudine/Tenofovir AlafenamideOriginator routesteps: 6total yield: 165 mg
2,3-dihydroxypropyl benzoate→2-oxoethyl benzoate→2,2-diethoxyethanethiol→(5-ethoxy-1,3-oxathiolan-2-yl)methyl benzoate→4-aminopyrimidin-2(1H)-one→((2R,5S)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate→benzothioic O-acid→2-bromo-1,1-diethoxyethane→S-(2,2-diethoxyethyl) benzothioate
Dolutegravir/Lamivudine/Tenofovir AlafenamideOptimised routesteps: 4total yield: /
2-oxoethyl benzoate→((2R,5S)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate→(S)-2-hydroxy-3-mercaptopropanoic acid→(2R,5S)-2-((benzoyloxy)methyl)-1,3-oxathiolane-5-carboxylic acid→((2R)-5-acetoxy-1,3-oxathiolan-2-yl)methyl benzoate
Dolutegravir/Lamivudine/Tenofovir AlafenamideOptimised routesteps: 3total yield: /
2-oxoethyl benzoate→((2R)-5-acetoxy-1,3-oxathiolan-2-yl)methyl benzoate→1,4-dithiane-2,5-diol→N-(trimethylsilyl)-N-(2-((trimethylsilyl)oxy)pyrimidin-4-yl)acetamide→((2R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate
Lamivudine/Tenofovir Disoproxil FumarateOriginator routesteps: 6total yield: 165 mg
2,3-dihydroxypropyl benzoate→2-oxoethyl benzoate→2,2-diethoxyethanethiol→(5-ethoxy-1,3-oxathiolan-2-yl)methyl benzoate→4-aminopyrimidin-2(1H)-one→((2R,5S)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate→benzothioic O-acid→2-bromo-1,1-diethoxyethane→S-(2,2-diethoxyethyl) benzothioate
Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 4total yield: /
2-oxoethyl benzoate→((2R,5S)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate→(S)-2-hydroxy-3-mercaptopropanoic acid→(2R,5S)-2-((benzoyloxy)methyl)-1,3-oxathiolane-5-carboxylic acid→((2R)-5-acetoxy-1,3-oxathiolan-2-yl)methyl benzoate
Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 3total yield: /
2-oxoethyl benzoate→((2R)-5-acetoxy-1,3-oxathiolan-2-yl)methyl benzoate→1,4-dithiane-2,5-diol→N-(trimethylsilyl)-N-(2-((trimethylsilyl)oxy)pyrimidin-4-yl)acetamide→((2R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate
Bictegravir/Emtricitabine/Tenofovir Alafenamide 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
Efavirenz/Lamivudine/Tenofovir Disoproxil FumarateOriginator routesteps: 6total yield: 165 mg
2,3-dihydroxypropyl benzoate→2-oxoethyl benzoate→2,2-diethoxyethanethiol→(5-ethoxy-1,3-oxathiolan-2-yl)methyl benzoate→4-aminopyrimidin-2(1H)-one→((2R,5S)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate→benzothioic O-acid→2-bromo-1,1-diethoxyethane→S-(2,2-diethoxyethyl) benzothioate
Efavirenz/Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 4total yield: /
2-oxoethyl benzoate→((2R,5S)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate→(S)-2-hydroxy-3-mercaptopropanoic acid→(2R,5S)-2-((benzoyloxy)methyl)-1,3-oxathiolane-5-carboxylic acid→((2R)-5-acetoxy-1,3-oxathiolan-2-yl)methyl benzoate
Efavirenz/Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 3total yield: /
2-oxoethyl benzoate→((2R)-5-acetoxy-1,3-oxathiolan-2-yl)methyl benzoate→1,4-dithiane-2,5-diol→N-(trimethylsilyl)-N-(2-((trimethylsilyl)oxy)pyrimidin-4-yl)acetamide→((2R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate
Emtricitabine/Tenofovir Alafenamide 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: 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
LamivudineOriginator routesteps: 6total yield: 165 mg
2,3-dihydroxypropyl benzoate→2-oxoethyl benzoate→2,2-diethoxyethanethiol→(5-ethoxy-1,3-oxathiolan-2-yl)methyl benzoate→4-aminopyrimidin-2(1H)-one→((2R,5S)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate→benzothioic O-acid→2-bromo-1,1-diethoxyethane→S-(2,2-diethoxyethyl) benzothioate
LamivudineOptimised routesteps: 4total yield: /
2-oxoethyl benzoate→((2R,5S)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate→(S)-2-hydroxy-3-mercaptopropanoic acid→(2R,5S)-2-((benzoyloxy)methyl)-1,3-oxathiolane-5-carboxylic acid→((2R)-5-acetoxy-1,3-oxathiolan-2-yl)methyl benzoate
LamivudineOptimised routesteps: 3total yield: /
2-oxoethyl benzoate→((2R)-5-acetoxy-1,3-oxathiolan-2-yl)methyl benzoate→1,4-dithiane-2,5-diol→N-(trimethylsilyl)-N-(2-((trimethylsilyl)oxy)pyrimidin-4-yl)acetamide→((2R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate
EmtricitabineOptimised 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
Plazomicin sulfateOptimised routesteps: 4total yield: /
benzyl (2,5-dioxopyrrolidin-1-yl) carbonate→D-Streptamine, O-3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1->6)-O-[2,3,4,6-tetradeoxy-...]-2-deoxy-N3-[(phenylmethoxy)carbonyl]-→(S)-2,5-dioxopyrrolidin-1-yl 4-(((benzyloxy)carbonyl)amino)-2-hydroxybutanoate→PLAZ-014→2-oxoethyl benzoate→2-((((2S,3R)-3-(((benzyloxy)carbonyl)amino)-2-(((1R,2S,3S,4R,6S)-6-(((benzyloxy)carbonyl)amino)-4-((S)-4-(((benzyloxy)carbonyl)amino)-2-hydroxybutanamido)-3-(((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-3,4-dihydro-2H-pyran-6-yl)methyl)amino)ethyl benzoate

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