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CAS 105876-28-6
(R)-3-((tert-butyldimethylsilyl)oxy)-4-cyanobutanoic acid(3R)-3-[[tert-Butyl(dimethyl)silyl]oxy]-4-cyanobutanoic acid
Codes: ATOR-026, Atorvastatin-060, ROSU-027
Application context (from source-drug indications)
Type 2 diabetesAtorvastatin Calcium Hydrate/Metformin HydrochlorideHyperlipidaemiaAtorvastatin Calcium Hydrate/Metformin HydrochlorideCardiac and vascular disordersAtorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilHypertensionAtorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilHyperlipidaemiaAtorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilHeart diseaseAtorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilHypertensionFimasartan potassium trihydrate/Rosuvastatin calciumDyslipidaemiaFimasartan potassium trihydrate/Rosuvastatin calciumHypertensionRosuvastatin Calcium/TelmisartanHyperlipidaemiaRosuvastatin Calcium/TelmisartanHypertensionAtorvastatin Calcium Hydrate/IrbesartanHyperlipidaemiaAtorvastatin Calcium Hydrate/IrbesartanHypercholesterolaemiaAtorvastatin Calcium Hydrate/RamiprilHypertensionAtorvastatin Calcium Hydrate/RamiprilHyperlipidaemiaAtorvastatin strontiumSubarachnoid haemorrhageAtorvastatin strontiumHypertensionAtorvastatin strontiumHyperlipoproteinaemia type IIIAtorvastatin Calcium HydrateHyperlipidaemiaAtorvastatin Calcium HydrateHeterozygous familial hypercholesterolaemiaAtorvastatin Calcium HydrateHeart failureAtorvastatin Calcium HydrateType 2 diabetesAtorvastatin Calcium HydrateStrokeAtorvastatin Calcium HydrateHomozygous familial hypercholesterolaemiaRosuvastatin CalciumHeterozygous familial hypercholesterolaemiaRosuvastatin CalciumHyperlipoproteinaemia type IIIRosuvastatin CalciumAtherosclerosisRosuvastatin CalciumHyperlipoproteinaemia type IIRosuvastatin CalciumHypercholesterolaemiaRosuvastatin Calcium
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Atorvastatin Calcium Hydrate/Metformin Hydrochloride | Tier C — Watch / trade | - |
| Atorvastatin/Hydrochlorothiazide/Aspirin/Enalapril | Tier C — Watch / trade | - |
| Fimasartan potassium trihydrate/Rosuvastatin calcium | Tier C — Watch / trade | - |
| Rosuvastatin Calcium/Telmisartan | Tier C — Watch / trade | - |
| Atorvastatin Calcium Hydrate/Irbesartan | Tier C — Watch / trade | - |
| Atorvastatin Calcium Hydrate/Ramipril | Tier C — Watch / trade | - |
| Atorvastatin strontium | Tier C — Watch / trade | - |
| Atorvastatin Calcium Hydrate | Tier B — Position early | - |
| Rosuvastatin Calcium | 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.
sodium (3R,5R)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate→2,2-dimethoxypropane→2-(2-(4-fluorophenyl)-2-oxo-1-phenylethyl)-4-methyl-3-oxo-N-phenylpentanamide→(R)-3-((tert-butyldimethylsilyl)oxy)-4-cyanobutanoic acid→monomagnesium mono(3-(tert-butoxy)-3-oxopropanoate)→(R)-tert-butyl 5-((tert-butyldimethylsilyl)oxy)-6-cyano-3-oxohexanoate→(3R,5R)-tert-butyl 6-cyano-3,5-dihydroxyhexanoate→tert-butyl 2-((4R,6R)-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate→tert-butyl 2-((4R,6R)-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate→tert-butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate→(3R,5R)-tert-butyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate
Atorvastatin/Hydrochlorothiazide/Aspirin/EnalaprilOptimised routesteps: 4total yield: 41.5g(Atorvastatin-047)
4-Cyano-3(R)-hydroxybutyric acid methyl ester→3(R)-[tert-Butyl(dimethyl)silyloxy]-4-cyanobutyric acid methyl ester→(3R)-3-[[tert-Butyl(dimethyl)silyl]oxy]-4-cyanobutanoic acid→3(R)-[tert-Butyl(dimethyl)silyloxy]-5-hydroxypentanenitrile→5-Amino-3(R)-[tert-butyl(dimethyl)silyloxy]pentan-1-ol
N-(4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide→sodium (3R,5S,E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3,5-dihydroxyhept-6-enoate→ethyl (R)-4-cyano-3-hydroxybutanoate→ethyl (R)-3-((tert-butyldimethylsilyl)oxy)-4-cyanobutanoate→(R)-3-((tert-butyldimethylsilyl)oxy)-4-cyanobutanoic acid→tert-butyl (R)-3-((tert-butyldimethylsilyl)oxy)-4-cyanobutanoate→tert-butyl (R)-5-amino-3-((tert-butyldimethylsilyl)oxy)-5-oxopentanoate→(R)-5-(tert-butoxy)-3-((tert-butyldimethylsilyl)oxy)-5-oxopentanoic acid→methyl carbonochloridate→(S)-(R)-5-(tert-butoxy)-3-((tert-butyldimethylsilyl)oxy)-5-oxopentanoic (ethyl carbonic) anhydride→methyltriphenylphosphonium bromide→tert-butyl (R)-3-((tert-butyldimethylsilyl)oxy)-5-oxo-6-(triphenyl-l5-phosphanylidene)hexanoate→tert-butyl (R,E)-3-((tert-butyldimethylsilyl)oxy)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-5-oxohept-6-enoate→tert-butyl (R,E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3-hydroxy-5-oxohept-6-enoate→tert-butyl (3R,5S,E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3,5-dihydroxyhept-6-enoate
N-(4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide→sodium (3R,5S,E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3,5-dihydroxyhept-6-enoate→ethyl (R)-4-cyano-3-hydroxybutanoate→ethyl (R)-3-((tert-butyldimethylsilyl)oxy)-4-cyanobutanoate→(R)-3-((tert-butyldimethylsilyl)oxy)-4-cyanobutanoic acid→tert-butyl (R)-3-((tert-butyldimethylsilyl)oxy)-4-cyanobutanoate→tert-butyl (R)-5-amino-3-((tert-butyldimethylsilyl)oxy)-5-oxopentanoate→(R)-5-(tert-butoxy)-3-((tert-butyldimethylsilyl)oxy)-5-oxopentanoic acid→methyl carbonochloridate→(S)-(R)-5-(tert-butoxy)-3-((tert-butyldimethylsilyl)oxy)-5-oxopentanoic (ethyl carbonic) anhydride→methyltriphenylphosphonium bromide→tert-butyl (R)-3-((tert-butyldimethylsilyl)oxy)-5-oxo-6-(triphenyl-l5-phosphanylidene)hexanoate→tert-butyl (R,E)-3-((tert-butyldimethylsilyl)oxy)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-5-oxohept-6-enoate→tert-butyl (R,E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3-hydroxy-5-oxohept-6-enoate→tert-butyl (3R,5S,E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3,5-dihydroxyhept-6-enoate
sodium (3R,5R)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate→2,2-dimethoxypropane→2-(2-(4-fluorophenyl)-2-oxo-1-phenylethyl)-4-methyl-3-oxo-N-phenylpentanamide→(R)-3-((tert-butyldimethylsilyl)oxy)-4-cyanobutanoic acid→monomagnesium mono(3-(tert-butoxy)-3-oxopropanoate)→(R)-tert-butyl 5-((tert-butyldimethylsilyl)oxy)-6-cyano-3-oxohexanoate→(3R,5R)-tert-butyl 6-cyano-3,5-dihydroxyhexanoate→tert-butyl 2-((4R,6R)-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate→tert-butyl 2-((4R,6R)-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate→tert-butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate→(3R,5R)-tert-butyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate
sodium (3R,5R)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate→2,2-dimethoxypropane→2-(2-(4-fluorophenyl)-2-oxo-1-phenylethyl)-4-methyl-3-oxo-N-phenylpentanamide→(R)-3-((tert-butyldimethylsilyl)oxy)-4-cyanobutanoic acid→monomagnesium mono(3-(tert-butoxy)-3-oxopropanoate)→(R)-tert-butyl 5-((tert-butyldimethylsilyl)oxy)-6-cyano-3-oxohexanoate→(3R,5R)-tert-butyl 6-cyano-3,5-dihydroxyhexanoate→tert-butyl 2-((4R,6R)-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate→tert-butyl 2-((4R,6R)-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate→tert-butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate→(3R,5R)-tert-butyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate
4-Cyano-3(R)-hydroxybutyric acid methyl ester→3(R)-[tert-Butyl(dimethyl)silyloxy]-4-cyanobutyric acid methyl ester→(3R)-3-[[tert-Butyl(dimethyl)silyl]oxy]-4-cyanobutanoic acid→3(R)-[tert-Butyl(dimethyl)silyloxy]-5-hydroxypentanenitrile→5-Amino-3(R)-[tert-butyl(dimethyl)silyloxy]pentan-1-ol
sodium (3R,5R)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate→2,2-dimethoxypropane→2-(2-(4-fluorophenyl)-2-oxo-1-phenylethyl)-4-methyl-3-oxo-N-phenylpentanamide→(R)-3-((tert-butyldimethylsilyl)oxy)-4-cyanobutanoic acid→monomagnesium mono(3-(tert-butoxy)-3-oxopropanoate)→(R)-tert-butyl 5-((tert-butyldimethylsilyl)oxy)-6-cyano-3-oxohexanoate→(3R,5R)-tert-butyl 6-cyano-3,5-dihydroxyhexanoate→tert-butyl 2-((4R,6R)-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate→tert-butyl 2-((4R,6R)-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate→tert-butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate→(3R,5R)-tert-butyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate
N-(4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide→sodium (3R,5S,E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3,5-dihydroxyhept-6-enoate→ethyl (R)-4-cyano-3-hydroxybutanoate→ethyl (R)-3-((tert-butyldimethylsilyl)oxy)-4-cyanobutanoate→(R)-3-((tert-butyldimethylsilyl)oxy)-4-cyanobutanoic acid→tert-butyl (R)-3-((tert-butyldimethylsilyl)oxy)-4-cyanobutanoate→tert-butyl (R)-5-amino-3-((tert-butyldimethylsilyl)oxy)-5-oxopentanoate→(R)-5-(tert-butoxy)-3-((tert-butyldimethylsilyl)oxy)-5-oxopentanoic acid→methyl carbonochloridate→(S)-(R)-5-(tert-butoxy)-3-((tert-butyldimethylsilyl)oxy)-5-oxopentanoic (ethyl carbonic) anhydride→methyltriphenylphosphonium bromide→tert-butyl (R)-3-((tert-butyldimethylsilyl)oxy)-5-oxo-6-(triphenyl-l5-phosphanylidene)hexanoate→tert-butyl (R,E)-3-((tert-butyldimethylsilyl)oxy)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-5-oxohept-6-enoate→tert-butyl (R,E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3-hydroxy-5-oxohept-6-enoate→tert-butyl (3R,5S,E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3,5-dihydroxyhept-6-enoate
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