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CAS 147126-65-6

(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate(2S,5R)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate

Codes: LAMI-018, LAMI-018-a

Application context (from source-drug indications)

HIV infectionDolutegravir/Lamivudine/Tenofovir AlafenamideHIV infectionLamivudine/Tenofovir Disoproxil FumarateChronic hepatitis BLamivudine/Tenofovir Disoproxil FumarateHIV infectionEfavirenz/Lamivudine/Tenofovir Disoproxil FumarateHepatitis BLamivudineChronic hepatitis BLamivudineHIV infectionLamivudineRett syndromeLamivudineAlzheimer's diseaseLamivudineRetinal detachmentLamivudine

Source drugs (routes using this intermediate)

DrugTierExpiry
Dolutegravir/Lamivudine/Tenofovir AlafenamideTier C — Watch / trade-
Lamivudine/Tenofovir Disoproxil FumarateTier C — Watch / trade-
Efavirenz/Lamivudine/Tenofovir Disoproxil FumarateTier C — Watch / trade-
LamivudineTier 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 AlafenamideOptimised routesteps: 5total yield: /
4-aminopyrimidin-2(1H)-one→(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→2-oxoacetic acid hydrate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-oxoacetate→1,4-dithiane-2,5-diol→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate
Dolutegravir/Lamivudine/Tenofovir AlafenamideOptimised routesteps: 5total yield: /
(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate→2-mercaptoacetic acid→2-oxoacetic acid→5-oxo-1,3-oxathiolane-2-carboxylic acid→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-oxo-1,3-oxathiolane-2-carboxylate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate→(2S,5R)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate
Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 5total yield: /
4-aminopyrimidin-2(1H)-one→(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→2-oxoacetic acid hydrate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-oxoacetate→1,4-dithiane-2,5-diol→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate
Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 5total yield: /
(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate→2-mercaptoacetic acid→2-oxoacetic acid→5-oxo-1,3-oxathiolane-2-carboxylic acid→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-oxo-1,3-oxathiolane-2-carboxylate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate→(2S,5R)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate
Efavirenz/Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 5total yield: /
4-aminopyrimidin-2(1H)-one→(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→2-oxoacetic acid hydrate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-oxoacetate→1,4-dithiane-2,5-diol→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate
Efavirenz/Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 5total yield: /
(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate→2-mercaptoacetic acid→2-oxoacetic acid→5-oxo-1,3-oxathiolane-2-carboxylic acid→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-oxo-1,3-oxathiolane-2-carboxylate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate→(2S,5R)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate
LamivudineOptimised routesteps: 5total yield: /
4-aminopyrimidin-2(1H)-one→(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→2-oxoacetic acid hydrate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-oxoacetate→1,4-dithiane-2,5-diol→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolane-2-carboxylate
LamivudineOptimised routesteps: 5total yield: /
(1R,2S,5R)-2-isopropyl-5-methylcyclohexan-1-ol→(2R,5S)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate→2-mercaptoacetic acid→2-oxoacetic acid→5-oxo-1,3-oxathiolane-2-carboxylic acid→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-oxo-1,3-oxathiolane-2-carboxylate→(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-hydroxy-1,3-oxathiolane-2-carboxylate→(2S,5R)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 5-acetoxy-1,3-oxathiolane-2-carboxylate

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