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CAS 79-33-4

2(S)-Hydroxypropionic acid(2S)-2-Hydroxypropanoic acid

Codes: Tenofovir disoproxil phosphate-032, (XIII)955428-1-a

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 phosphatePeripheral T-cell lymphomaGolidocitinibEB病毒感染GolidocitinibViral infectionGolidocitinibHistiocytosisGolidocitinib噬血细胞性淋巴组织细胞增多症GolidocitinibInterstitial lung diseaseGolidocitinib

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-
GolidocitinibTier 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: 8total yield: 1.97g(Tenofovir disoproxil phosphate-013)
2(R)-Methyloxirane→(R)-1,2-Propanediol→2(S)-Hydroxypropionic acid→Methyl (2S)-2-hydroxypropanoate→Methyl (2S)-2-[(methanesulfonyl)oxy]propanoate→(2S)-1-Hydroxypropan-2-yl methanesulfonate→(2R)-2-Hydroxypropanoic acid→D-Lactic acid methyl ester→(2R)-2-Hydroxypropyl 4-methylbenzene-1-sulfonate
Efavirenz/Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 8total yield: 1.97g(Tenofovir disoproxil phosphate-013)
2(R)-Methyloxirane→(R)-1,2-Propanediol→2(S)-Hydroxypropionic acid→Methyl (2S)-2-hydroxypropanoate→Methyl (2S)-2-[(methanesulfonyl)oxy]propanoate→(2S)-1-Hydroxypropan-2-yl methanesulfonate→(2R)-2-Hydroxypropanoic acid→D-Lactic acid methyl ester→(2R)-2-Hydroxypropyl 4-methylbenzene-1-sulfonate
Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateOptimised routesteps: 8total yield: 1.97g(Tenofovir disoproxil phosphate-013)
2(R)-Methyloxirane→(R)-1,2-Propanediol→2(S)-Hydroxypropionic acid→Methyl (2S)-2-hydroxypropanoate→Methyl (2S)-2-[(methanesulfonyl)oxy]propanoate→(2S)-1-Hydroxypropan-2-yl methanesulfonate→(2R)-2-Hydroxypropanoic acid→D-Lactic acid methyl ester→(2R)-2-Hydroxypropyl 4-methylbenzene-1-sulfonate
Tenofovir disoproxil phosphateOptimised routesteps: 8total yield: 1.97g(Tenofovir disoproxil phosphate-013)
2(R)-Methyloxirane→(R)-1,2-Propanediol→2(S)-Hydroxypropionic acid→Methyl (2S)-2-hydroxypropanoate→Methyl (2S)-2-[(methanesulfonyl)oxy]propanoate→(2S)-1-Hydroxypropan-2-yl methanesulfonate→(2R)-2-Hydroxypropanoic acid→D-Lactic acid methyl ester→(2R)-2-Hydroxypropyl 4-methylbenzene-1-sulfonate
GolidocitinibOptimised routesteps: 8total yield: /
7-Nitro-1H-indole→1-(4-Methylbenzene-1-sulfonyl)-7-nitro-1H-indole→3-Bromo-1-(4-methylbenzene-1-sulfonyl)-7-nitro-1H-indole→1-(4-Methylbenzene-1-sulfonyl)-7-nitro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole→2-Chloropyrimidin-4-yl chloride→3-(2-Chloro-4-pyrimidinyl)-N-tosyl-7-nitroindole→3-(2-Chloro-4-pyrimidinyl)-7-nitroindole→3-Methoxy-1-methyl-1H-pyrazol-4-amine hydrogen chloride (1/2)→N-(3-Methoxy-1-methyl-1H-pyrazol-4-yl)-4-(7-nitro-1H-indol-3-yl)pyrimidin-2-amine→3-[2-[(3-Methoxy-1-methyl-1H-pyrazol-4-yl)amino]pyrimidin-4-yl]-1H-indol-7-amine→(2R)-2-(4-Methylpiperazin-1-yl)propanoic acid hydrogen chloride (1/2)→1-Methylpiperazine→(2S)-2-Hydroxypropanoic acid

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