CAS 113-00-8

Guanidineguanidine

Codes: Tenofovir disoproxil phosphate-045, PEME-024

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 phosphateNon-small cell lung cancerPemetrexed Disodium Hydrate间皮组织肿瘤Pemetrexed Disodium Hydrate胸膜孤立性纤维瘤Pemetrexed Disodium HydrateBladder cancerPemetrexed Disodium HydrateUrothelial carcinomaPemetrexed Disodium HydrateSolid tumourPemetrexed Disodium Hydrate

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	-
Pemetrexed Disodium Hydrate	Tier B — Position early	-

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: 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

Efavirenz/Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 3total yield: /

Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateOptimised routesteps: 3total yield: /

Tenofovir disoproxil phosphateOptimised routesteps: 3total yield: /

Pemetrexed Disodium HydrateOptimised routesteps: 6total yield: 201 mg

dimethyl (4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoyl)-L-glutamate→4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid→ethyl 4-(3-oxopropyl)benzoate→3-ethylbenzo[d]thiazol-3-ium bromide→ethyl 4-(4-hydroxy-3-oxobutyl)benzoate→malononitrile→ethyl 4-(2-(5-amino-4-cyanofuran-3-yl)ethyl)benzoate→guanidine→ethyl 4-(2-(2,4-diamino-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoate→(S)-diethyl 2-aminopentanedioate

Pemetrexed Disodium HydrateOptimised routesteps: 9total yield: /

guanidine→1-phenylethan-1-amine→methyl carbonochloridate→methyl (1-phenylethyl)carbamate→(E)-1-bromobut-2-ene→methyl (E)-but-2-en-1-yl(1-phenylethyl)carbamate→(E)-N-(1-phenylethyl)but-2-en-1-amine→dimethyl malonate→methyl (E)-3-(but-2-en-1-yl(1-phenylethyl)amino)-3-oxopropanoate→methyl 2-oxo-1-(1-phenylethyl)-4-vinylpyrrolidine-3-carboxylate→methyl 1-(1-phenylethyl)-2-thioxo-4-vinylpyrrolidine-3-carboxylate→2-amino-7-(1-phenylethyl)-5-vinyl-3,5,6,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one→diethyl (4-iodobenzoyl)-L-glutamate→diethyl (4-(2-(2-amino-4-oxo-7-(1-phenylethyl)-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoyl)-L-glutamate

Intermediates available on this site

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