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CAS 180587-75-1
(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine
Codes: Tenofovir disoproxil phosphate-009
Application context (from source-drug indications)
HIV infectionLamivudine/Tenofovir Disoproxil FumarateChronic hepatitis BLamivudine/Tenofovir Disoproxil FumarateHIV infectionEfavirenz/Lamivudine/Tenofovir Disoproxil FumarateHIV infectionEmtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateHepatitis BTenofovir disoproxil phosphate
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Lamivudine/Tenofovir Disoproxil Fumarate | Tier C — Watch / trade | - |
| Efavirenz/Lamivudine/Tenofovir Disoproxil Fumarate | Tier C — Watch / trade | - |
| Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil Fumarate | Tier B — Position early | - |
| Tenofovir disoproxil phosphate | 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.
Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 11total yield: 23.3g(Tenofovir disoproxil phosphate (API))
Chloroacetyl chloride→1-Chloro-2(R)-propanol→Diethyl (tosyloxy)methylphosphonate→Diethyl (chloromethyl)phosphonate→Diethyl phosphonate→Diethyl phosphonomethanol→Diethyl (2-chloro-1(R)-methylethoxy)methylphosphonate→6-Aminopurine→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→(R)-9-(2-Phosphonomethoxypropyl)adenine→Chloromethyl isopropyl carbonate→Bis[[(isopropoxycarbonyl)oxy]methyl] ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→2(R)-Methyloxirane→(R)-(+)-9-(2-Hydroxypropyl)adenine→(R)-Propylene carbonate→(S)-Glycidol→(R)-1,2-Propanediol
Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 8total yield: 21.8g(Tenofovir disoproxil phosphate-009)
Diethyl phosphonate→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→(R)-(+)-9-(2-Hydroxypropyl)adenine→(2R)-1-(6-Chloro-9H-purin-9-yl)propan-2-ol→6-Chloro-9H-purine→1-Bromopropan-2-one→1-(6-Chloro-9H-purin-9-yl)acetone→Diethoxyphosphoryl)methyl triflate→Diethyl [2-(6-chloropurin-9-yl)-1(R)-methylethyloxy]methylphosphonate→1-(6-Amino-9H-purin-9-yl)acetone
Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 3total yield: 21.8g(Tenofovir disoproxil phosphate-009)
(R)-1-(6-Amino-9H-purin-9-yl)propan-2-ol→(Diethoxyphosphoryl)methyl 4-methylbenzene-1-sulfonate→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→Carbamide→Thiocarbamide→Guanidine→Ethoxy(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→(Ethylsulfanyl)(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→(Ethylamino)(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate
Efavirenz/Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 11total yield: 23.3g(Tenofovir disoproxil phosphate (API))
Chloroacetyl chloride→1-Chloro-2(R)-propanol→Diethyl (tosyloxy)methylphosphonate→Diethyl (chloromethyl)phosphonate→Diethyl phosphonate→Diethyl phosphonomethanol→Diethyl (2-chloro-1(R)-methylethoxy)methylphosphonate→6-Aminopurine→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→(R)-9-(2-Phosphonomethoxypropyl)adenine→Chloromethyl isopropyl carbonate→Bis[[(isopropoxycarbonyl)oxy]methyl] ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→2(R)-Methyloxirane→(R)-(+)-9-(2-Hydroxypropyl)adenine→(R)-Propylene carbonate→(S)-Glycidol→(R)-1,2-Propanediol
Efavirenz/Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 8total yield: 21.8g(Tenofovir disoproxil phosphate-009)
Diethyl phosphonate→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→(R)-(+)-9-(2-Hydroxypropyl)adenine→(2R)-1-(6-Chloro-9H-purin-9-yl)propan-2-ol→6-Chloro-9H-purine→1-Bromopropan-2-one→1-(6-Chloro-9H-purin-9-yl)acetone→Diethoxyphosphoryl)methyl triflate→Diethyl [2-(6-chloropurin-9-yl)-1(R)-methylethyloxy]methylphosphonate→1-(6-Amino-9H-purin-9-yl)acetone
Efavirenz/Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 3total yield: 21.8g(Tenofovir disoproxil phosphate-009)
(R)-1-(6-Amino-9H-purin-9-yl)propan-2-ol→(Diethoxyphosphoryl)methyl 4-methylbenzene-1-sulfonate→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→Carbamide→Thiocarbamide→Guanidine→Ethoxy(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→(Ethylsulfanyl)(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→(Ethylamino)(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate
Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateOptimised routesteps: 11total yield: 23.3g(Tenofovir disoproxil phosphate (API))
Chloroacetyl chloride→1-Chloro-2(R)-propanol→Diethyl (tosyloxy)methylphosphonate→Diethyl (chloromethyl)phosphonate→Diethyl phosphonate→Diethyl phosphonomethanol→Diethyl (2-chloro-1(R)-methylethoxy)methylphosphonate→6-Aminopurine→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→(R)-9-(2-Phosphonomethoxypropyl)adenine→Chloromethyl isopropyl carbonate→Bis[[(isopropoxycarbonyl)oxy]methyl] ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→2(R)-Methyloxirane→(R)-(+)-9-(2-Hydroxypropyl)adenine→(R)-Propylene carbonate→(S)-Glycidol→(R)-1,2-Propanediol
Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateOptimised routesteps: 8total yield: 21.8g(Tenofovir disoproxil phosphate-009)
Diethyl phosphonate→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→(R)-(+)-9-(2-Hydroxypropyl)adenine→(2R)-1-(6-Chloro-9H-purin-9-yl)propan-2-ol→6-Chloro-9H-purine→1-Bromopropan-2-one→1-(6-Chloro-9H-purin-9-yl)acetone→Diethoxyphosphoryl)methyl triflate→Diethyl [2-(6-chloropurin-9-yl)-1(R)-methylethyloxy]methylphosphonate→1-(6-Amino-9H-purin-9-yl)acetone
Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateOptimised routesteps: 3total yield: 21.8g(Tenofovir disoproxil phosphate-009)
Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateOptimised routesteps: 3total yield: /
(R)-1-(6-Amino-9H-purin-9-yl)propan-2-ol→(Diethoxyphosphoryl)methyl 4-methylbenzene-1-sulfonate→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→Carbamide→Thiocarbamide→Guanidine→Ethoxy(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→(Ethylsulfanyl)(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→(Ethylamino)(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate
Tenofovir disoproxil phosphateOptimised routesteps: 11total yield: 23.3g(Tenofovir disoproxil phosphate (API))
Chloroacetyl chloride→1-Chloro-2(R)-propanol→Diethyl (tosyloxy)methylphosphonate→Diethyl (chloromethyl)phosphonate→Diethyl phosphonate→Diethyl phosphonomethanol→Diethyl (2-chloro-1(R)-methylethoxy)methylphosphonate→6-Aminopurine→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→(R)-9-(2-Phosphonomethoxypropyl)adenine→Chloromethyl isopropyl carbonate→Bis[[(isopropoxycarbonyl)oxy]methyl] ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→2(R)-Methyloxirane→(R)-(+)-9-(2-Hydroxypropyl)adenine→(R)-Propylene carbonate→(S)-Glycidol→(R)-1,2-Propanediol
Tenofovir disoproxil phosphateOptimised routesteps: 8total yield: 21.8g(Tenofovir disoproxil phosphate-009)
Diethyl phosphonate→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→(R)-(+)-9-(2-Hydroxypropyl)adenine→(2R)-1-(6-Chloro-9H-purin-9-yl)propan-2-ol→6-Chloro-9H-purine→1-Bromopropan-2-one→1-(6-Chloro-9H-purin-9-yl)acetone→Diethoxyphosphoryl)methyl triflate→Diethyl [2-(6-chloropurin-9-yl)-1(R)-methylethyloxy]methylphosphonate→1-(6-Amino-9H-purin-9-yl)acetone
Tenofovir disoproxil phosphateOptimised routesteps: 3total yield: 21.8g(Tenofovir disoproxil phosphate-009)
(R)-1-(6-Amino-9H-purin-9-yl)propan-2-ol→(Diethoxyphosphoryl)methyl 4-methylbenzene-1-sulfonate→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→Carbamide→Thiocarbamide→Guanidine→Ethoxy(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→(Ethylsulfanyl)(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→(Ethylamino)(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate
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