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CAS 180587-74-0

(2R)-1-(6-Chloro-9H-purin-9-yl)propan-2-ol

Codes: Tenofovir disoproxil phosphate-022

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)

DrugTierExpiry
Lamivudine/Tenofovir Disoproxil FumarateTier C — Watch / trade-
Efavirenz/Lamivudine/Tenofovir Disoproxil FumarateTier C — Watch / trade-
Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateTier B — Position early-
Tenofovir disoproxil phosphateTier 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: 4total yield: 1.7g(Tenofovir disoproxil phosphate-014)
(R)-(+)-9-(2-Hydroxypropyl)adenine→(R)-Propylene carbonate→6-Chloro-5-nitropyrimidin-4-amine→(2R)-1-[(6-Chloro-5-nitropyrimidin-4-yl)amino]propan-2-ol→4,6-Dichloro-5-nitropyrimidine→(2R)-1-Aminopropan-2-ol→(2R)-1-(6-Chloro-9H-purin-9-yl)propan-2-ol
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: 4total yield: 1.7g(Tenofovir disoproxil phosphate-014)
(R)-(+)-9-(2-Hydroxypropyl)adenine→(R)-Propylene carbonate→6-Chloro-5-nitropyrimidin-4-amine→(2R)-1-[(6-Chloro-5-nitropyrimidin-4-yl)amino]propan-2-ol→4,6-Dichloro-5-nitropyrimidine→(2R)-1-Aminopropan-2-ol→(2R)-1-(6-Chloro-9H-purin-9-yl)propan-2-ol
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
Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateOptimised routesteps: 4total yield: 1.7g(Tenofovir disoproxil phosphate-014)
(R)-(+)-9-(2-Hydroxypropyl)adenine→(R)-Propylene carbonate→6-Chloro-5-nitropyrimidin-4-amine→(2R)-1-[(6-Chloro-5-nitropyrimidin-4-yl)amino]propan-2-ol→4,6-Dichloro-5-nitropyrimidine→(2R)-1-Aminopropan-2-ol→(2R)-1-(6-Chloro-9H-purin-9-yl)propan-2-ol
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
Tenofovir disoproxil phosphateOptimised routesteps: 4total yield: 1.7g(Tenofovir disoproxil phosphate-014)
(R)-(+)-9-(2-Hydroxypropyl)adenine→(R)-Propylene carbonate→6-Chloro-5-nitropyrimidin-4-amine→(2R)-1-[(6-Chloro-5-nitropyrimidin-4-yl)amino]propan-2-ol→4,6-Dichloro-5-nitropyrimidine→(2R)-1-Aminopropan-2-ol→(2R)-1-(6-Chloro-9H-purin-9-yl)propan-2-ol
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

Intermediates available on this site

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