Product Name

  • Name

    tert-Butyl rosuvastatin

  • EINECS 609-144-4
  • CAS No. 355806-00-7
  • Article Data29
  • CAS DataBase
  • Density 1.26 g/cm3
  • Solubility
  • Melting Point
  • Formula C26H36FN3O6S
  • Boiling Point 704.158 °C at 760 mmHg
  • Molecular Weight 537.653
  • Flash Point 379.661 °C
  • Transport Information
  • Appearance white to off-white crystal powder
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 355806-00-7 (tert-Butyl rosuvastatin)
  • Hazard Symbols
  • Synonyms (3R,5S,6E)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-[(methanesulfonyl)methylamino]pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoicacid tert-butyl ester;Rosuvastatin tert-butyl ester;tert-Butyl(6E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl]-(3R,5S)-3,5-dihydroxyhept-6-enoate;6-Heptenoic acid,7-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-3,5-dihydroxy-,1,1-dimethylethyl ester, (3R,5S,6E)-;
  • PSA 138.30000
  • LogP 4.73960

Synthetic route

2-[(4R,6S)-6-[(E)-2-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidin-5-yl]vinyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid tert butyl ester
289042-12-2

2-[(4R,6S)-6-[(E)-2-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidin-5-yl]vinyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid tert butyl ester

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; water at 10℃; for 4h; Temperature;95%
With water; trifluoroacetic acid at 30 - 40℃;86%
With camphor-10-sulfonic acid In water; acetonitrile at 20℃; for 0.5h;57%
tert-butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2-phenyl-1,3-dioxan-4-yl)acetate
1235588-97-2

tert-butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2-phenyl-1,3-dioxan-4-yl)acetate

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Stage #1: tert-butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2-phenyl-1,3-dioxan-4-yl)acetate With water; acetic acid at 40 - 60℃; for 3h;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate		95%
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 1h;95%
tert-butyl 2-((2R,4S)-4-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-1,5-dioxaspiro[5.5]undecan-2-yl)acetate

tert-butyl 2-((2R,4S)-4-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-1,5-dioxaspiro[5.5]undecan-2-yl)acetate

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 1h;95%
tert-butyl 2-((7R,9S)-9-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-6,10-dioxaspiro[4.5]decan-7-yl)acetate

tert-butyl 2-((7R,9S)-9-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-6,10-dioxaspiro[4.5]decan-7-yl)acetate

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 1h;95%
(+)-(3R)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-3-hydroxy-5-oxo-(6E)-heptenoic acid tert-butyl ester

(+)-(3R)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-3-hydroxy-5-oxo-(6E)-heptenoic acid tert-butyl ester

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Stage #1: (+)-(3R)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-3-hydroxy-5-oxo-(6E)-heptenoic acid tert-butyl ester With triethyl borane In tetrahydrofuran; methanol at -78℃; for 0.25h; Inert atmosphere;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol at -78℃; for 0.5h; Inert atmosphere;		90.6%
Stage #1: (+)-(3R)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-3-hydroxy-5-oxo-(6E)-heptenoic acid tert-butyl ester With diethyl methoxy borane In tetrahydrofuran; methanol at -78℃; for 0.5h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol for 3h;		86%
With sodium hydroxide; water In ethanol at 20℃; for 2h;
With sodium tetrahydroborate; diethyl methoxy borane In tetrahydrofuran; methanol at -78 - -75℃; for 1.5h;10.5 g
tert-butyl (6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidin-5-yl]-3,5-dioxohept-6-enoate

tert-butyl (6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidin-5-yl]-3,5-dioxohept-6-enoate

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
With glucose dehydrogenase; D-Glucose; carbonyl reductase; NADP; sodium carbonate In ethanol; water at 30 - 50℃; pH=6.9 - 7.2; Enzymatic reaction;86.7%
tert-butyl-6-[(1E)-2-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetate
1007871-85-3

tert-butyl-6-[(1E)-2-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetate

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Stage #1: tert-butyl-6-[(1E)-2-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetate With hydrogenchloride; water In tetrahydrofuran at 20℃; for 2.5h;
Stage #2: With sodium hydroxide; water In water at 0 - 15℃; pH=6; Product distribution / selectivity;		81%
Stage #1: tert-butyl-6-[(1E)-2-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetate With hydrogenchloride; water In tetrahydrofuran at 20℃; for 1 - 2.5h;
Stage #2: With sodium hydroxide In tetrahydrofuran; water at 15℃; pH=6; Product distribution / selectivity;		81%
(5S)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-5-(hydroxy)-3-oxo-(6E)-heptenoic acid tert-butyl ester
910867-13-9

(5S)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-5-(hydroxy)-3-oxo-(6E)-heptenoic acid tert-butyl ester

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Stage #1: (5S)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-5-(hydroxy)-3-oxo-(6E)-heptenoic acid tert-butyl ester With diethyl methoxy borane In tetrahydrofuran; methanol at -78℃; for 0.583333h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol at -78℃; for 3 - 4h;
Stage #3: With methanol; water; acetic acid In tetrahydrofuran; ethyl acetate at -78℃; for 0.166667h;
Stage #1: (5S)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-5-(hydroxy)-3-oxo-(6E)-heptenoic acid tert-butyl ester With diethyl methoxy borane In tetrahydrofuran; methanol at -78 - -75℃; for 1.16667h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol at -78 - -75℃; for 2.25h;
Stage #3: With acetic acid In tetrahydrofuran; methanol at -78℃;
Stage #1: (5S)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-5-(hydroxy)-3-oxo-(6E)-heptenoic acid tert-butyl ester With diethyl methoxy borane In tetrahydrofuran; methanol at -78 - -75℃; for 1.16667h; Inert atmosphere;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol at -78 - -75℃; Inert atmosphere;
Stage #1: (5S)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-5-(hydroxy)-3-oxo-(6E)-heptenoic acid tert-butyl ester With diethyl methoxy borane In tetrahydrofuran; methanol at -78℃; for 0.583333h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol at -78℃; for 3 - 4h;
Stage #3: With acetic acid In tetrahydrofuran; methanol; water; ethyl acetate at -78 - 28℃; for 0.166667h;
Stage #1: (5S)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-5-(hydroxy)-3-oxo-(6E)-heptenoic acid tert-butyl ester With sodium tetrahydroborate; diethyl methoxy borane In tetrahydrofuran; methanol at -90 - 85℃; for 14.5h;
Stage #2: With acetic acid In tetrahydrofuran; methanol
tert-butyl 2-[(4R,6S)-6-[(benzo[d]thiazol-2-ylsulfonyl)methyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate
1054627-26-7

tert-butyl 2-[(4R,6S)-6-[(benzo[d]thiazol-2-ylsulfonyl)methyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium tert-butylate / tetrahydrofuran / 1.75 h / -80 - 45 °C
2: hydrogenchloride; water / acetonitrile / 25 - 55 °C / pH 2.5
View Scheme
Multi-step reaction with 2 steps
1: sodium hydride / tetrahydrofuran / 0 - 35 °C
2: hydrogenchloride / water; acetonitrile / 35 - 40 °C
View Scheme
tert-butyl 2-[(4R,6S)-2,2-dimethyl-6-[(4-nitrophenylsulfonyloxy)methyl]-1,3-dioxan-4-yl]acetate
141942-89-4

tert-butyl 2-[(4R,6S)-2,2-dimethyl-6-[(4-nitrophenylsulfonyloxy)methyl]-1,3-dioxan-4-yl]acetate

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 4-methyl-morpholine / 80 - 90 °C
2: dihydrogen peroxide; hexaammonium heptamolybdate tetrahydrate / dichloromethane; isopropyl alcohol / 16.5 h / 0 - 30 °C
3: potassium tert-butylate / tetrahydrofuran / 1.75 h / -80 - 45 °C
4: hydrogenchloride; water / acetonitrile / 25 - 55 °C / pH 2.5
View Scheme
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0.5 h / 0 - 5 °C
1.2: 10 - 15 °C
2.1: potassium tert-butylate / tetrahydrofuran / 1.75 h / -80 - 45 °C
3.1: hydrogenchloride; water / acetonitrile / 25 - 55 °C / pH 2.5
View Scheme
Multi-step reaction with 5 steps
1: triethylamine / toluene / 3 h / 0 - 30 °C / Inert atmosphere
2: 4-methyl-morpholine / 80 - 90 °C
3: dihydrogen peroxide; hexaammonium heptamolybdate tetrahydrate / dichloromethane; isopropyl alcohol / 16.5 h / 0 - 30 °C
4: potassium tert-butylate / tetrahydrofuran / 1.75 h / -80 - 45 °C
5: hydrogenchloride; water / acetonitrile / 25 - 55 °C / pH 2.5
View Scheme
Multi-step reaction with 5 steps
1: triethylamine / dichloromethane
2: N,N-dimethyl-formamide / 25 - 130 °C
3: hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / isopropyl alcohol
4: sodium hydride / tetrahydrofuran / 0 - 35 °C
5: hydrogenchloride / water; acetonitrile / 35 - 40 °C
View Scheme
(4R,6S)-6-(benzothiazol-2-mercapto)methyl-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester
1353750-24-9

(4R,6S)-6-(benzothiazol-2-mercapto)methyl-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dihydrogen peroxide; hexaammonium heptamolybdate tetrahydrate / dichloromethane; isopropyl alcohol / 16.5 h / 0 - 30 °C
2: potassium tert-butylate / tetrahydrofuran / 1.75 h / -80 - 45 °C
3: hydrogenchloride; water / acetonitrile / 25 - 55 °C / pH 2.5
View Scheme
(R)-tert-butyl 4-cyano-3-(tert-butyldimethylsilyloxy)butyrate

(R)-tert-butyl 4-cyano-3-(tert-butyldimethylsilyloxy)butyrate

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: dihydrogen peroxide; sodium hydroxide / ethanol; water / 20 h / 10 - 30 °C
2.1: sodium hypochlorite / dichloromethane / 8 h / 0 - 5 °C
3.1: triethylamine / toluene / 4 h / -45 - 0 °C / Inert atmosphere
4.1: n-butyllithium / tetrahydrofuran / 1.5 h / -60 - 0 °C
4.2: 1.5 h / -60 - 0 °C
5.1: cyclohexane / 30 h / 20 - 82 °C
6.1: hydrogenchloride; water / methanol / 4.5 h / 10 - 25 °C
7.1: diethyl methoxy borane; sodium tetrahydroborate / methanol; tetrahydrofuran / 4 h / -80 - 25 °C / Inert atmosphere
View Scheme
(R)-tert-butyl 4-carbamoyl-3-(tert-butyldimethylsilyloxy)butyrate

(R)-tert-butyl 4-carbamoyl-3-(tert-butyldimethylsilyloxy)butyrate

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium hypochlorite / dichloromethane / 8 h / 0 - 5 °C
2.1: triethylamine / toluene / 4 h / -45 - 0 °C / Inert atmosphere
3.1: n-butyllithium / tetrahydrofuran / 1.5 h / -60 - 0 °C
3.2: 1.5 h / -60 - 0 °C
4.1: cyclohexane / 30 h / 20 - 82 °C
5.1: hydrogenchloride; water / methanol / 4.5 h / 10 - 25 °C
6.1: diethyl methoxy borane; sodium tetrahydroborate / methanol; tetrahydrofuran / 4 h / -80 - 25 °C / Inert atmosphere
View Scheme
(R)-5-tert-butoxy-3-(tert-butyldimethylsilyloxy)-5-oxopentanoic acid

(R)-5-tert-butoxy-3-(tert-butyldimethylsilyloxy)-5-oxopentanoic acid

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: triethylamine / toluene / 4 h / -45 - 0 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran / 1.5 h / -60 - 0 °C
2.2: 1.5 h / -60 - 0 °C
3.1: cyclohexane / 30 h / 20 - 82 °C
4.1: hydrogenchloride; water / methanol / 4.5 h / 10 - 25 °C
5.1: diethyl methoxy borane; sodium tetrahydroborate / methanol; tetrahydrofuran / 4 h / -80 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: dicyclohexyl-carbodiimide / dichloromethane / 25 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere
2.2: -78 °C / Inert atmosphere
3.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
3.2: 20 °C / Inert atmosphere
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere
5.1: triethyl borane / tetrahydrofuran; methanol / 0.25 h / -78 °C / Inert atmosphere
5.2: 0.5 h / -78 °C / Inert atmosphere
View Scheme
(R)-3-(tert-butyldimethylsilyloxy)-5-ethoxycarbonyloxy-5-oxopentanoic acid tert-butyl ester

(R)-3-(tert-butyldimethylsilyloxy)-5-ethoxycarbonyloxy-5-oxopentanoic acid tert-butyl ester

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: n-butyllithium / tetrahydrofuran / 1.5 h / -60 - 0 °C
1.2: 1.5 h / -60 - 0 °C
2.1: cyclohexane / 30 h / 20 - 82 °C
3.1: hydrogenchloride; water / methanol / 4.5 h / 10 - 25 °C
4.1: diethyl methoxy borane; sodium tetrahydroborate / methanol; tetrahydrofuran / 4 h / -80 - 25 °C / Inert atmosphere
View Scheme
(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 1H-imidazole / dichloromethane / 21 h / 20 - 30 °C
2.1: sodium hydroxide; water / methanol / 3 h / 0 - 15 °C
3.1: sodium hydroxide; dmap / tert-butyl alcohol / 8 - 30 °C
4.1: dihydrogen peroxide; sodium hydroxide / ethanol; water / 20 h / 10 - 30 °C
5.1: sodium hypochlorite / dichloromethane / 8 h / 0 - 5 °C
6.1: triethylamine / toluene / 4 h / -45 - 0 °C / Inert atmosphere
7.1: n-butyllithium / tetrahydrofuran / 1.5 h / -60 - 0 °C
7.2: 1.5 h / -60 - 0 °C
8.1: cyclohexane / 30 h / 20 - 82 °C
9.1: hydrogenchloride; water / methanol / 4.5 h / 10 - 25 °C
10.1: diethyl methoxy borane; sodium tetrahydroborate / methanol; tetrahydrofuran / 4 h / -80 - 25 °C / Inert atmosphere
View Scheme
tert-butyl (3R)-3-(tert-butyldimethylsilyloxy)-5-oxo-6-triphenylphosphorylidenehexanoate

tert-butyl (3R)-3-(tert-butyldimethylsilyloxy)-5-oxo-6-triphenylphosphorylidenehexanoate

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: cyclohexane / 30 h / 20 - 82 °C
2: hydrogenchloride; water / methanol / 4.5 h / 10 - 25 °C
3: diethyl methoxy borane; sodium tetrahydroborate / methanol; tetrahydrofuran / 4 h / -80 - 25 °C / Inert atmosphere
View Scheme
tertiary butyl 7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-(3R)-3-hydroxy-5-oxo-(E)-6-heptenoate

tertiary butyl 7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-(3R)-3-hydroxy-5-oxo-(E)-6-heptenoate

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
With sodium tetrahydroborate; diethyl methoxy borane In tetrahydrofuran; methanol at -80 - 25℃; for 4h; Inert atmosphere;
(R)-(-)-ethyl 4-cyano-3-(tert-butyldimethylsilyloxy)butyrate
141942-82-7

(R)-(-)-ethyl 4-cyano-3-(tert-butyldimethylsilyloxy)butyrate

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: sodium hydroxide; water / methanol / 3 h / 0 - 15 °C
2.1: sodium hydroxide; dmap / tert-butyl alcohol / 8 - 30 °C
3.1: dihydrogen peroxide; sodium hydroxide / ethanol; water / 20 h / 10 - 30 °C
4.1: sodium hypochlorite / dichloromethane / 8 h / 0 - 5 °C
5.1: triethylamine / toluene / 4 h / -45 - 0 °C / Inert atmosphere
6.1: n-butyllithium / tetrahydrofuran / 1.5 h / -60 - 0 °C
6.2: 1.5 h / -60 - 0 °C
7.1: cyclohexane / 30 h / 20 - 82 °C
8.1: hydrogenchloride; water / methanol / 4.5 h / 10 - 25 °C
9.1: diethyl methoxy borane; sodium tetrahydroborate / methanol; tetrahydrofuran / 4 h / -80 - 25 °C / Inert atmosphere
View Scheme
(R)-4-cyano-3-(tert-butyldimethylsilyloxy)butyric acid
105876-28-6

(R)-4-cyano-3-(tert-butyldimethylsilyloxy)butyric acid

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: sodium hydroxide; dmap / tert-butyl alcohol / 8 - 30 °C
2.1: dihydrogen peroxide; sodium hydroxide / ethanol; water / 20 h / 10 - 30 °C
3.1: sodium hypochlorite / dichloromethane / 8 h / 0 - 5 °C
4.1: triethylamine / toluene / 4 h / -45 - 0 °C / Inert atmosphere
5.1: n-butyllithium / tetrahydrofuran / 1.5 h / -60 - 0 °C
5.2: 1.5 h / -60 - 0 °C
6.1: cyclohexane / 30 h / 20 - 82 °C
7.1: hydrogenchloride; water / methanol / 4.5 h / 10 - 25 °C
8.1: diethyl methoxy borane; sodium tetrahydroborate / methanol; tetrahydrofuran / 4 h / -80 - 25 °C / Inert atmosphere
View Scheme
3-oxo-propionic acid tert-butyl ester
108350-21-6

3-oxo-propionic acid tert-butyl ester

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 25 - 30 °C
2: sodium hydroxide / ethanol; water / 25 - 30 °C
3: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide / water; dichloromethane / 5 - 10 °C
4: sodium carbonate; D-Glucose; NADP; glucose dehydrogenase; carbonyl reductase / ethanol; water / 30 - 50 °C / pH 6.9 - 7.2 / Enzymatic reaction
View Scheme
3-hydroxy-5-oxo-hexanoic acid t-butyl ester

3-hydroxy-5-oxo-hexanoic acid t-butyl ester

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / ethanol; water / 25 - 30 °C
2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide / water; dichloromethane / 5 - 10 °C
3: sodium carbonate; D-Glucose; NADP; glucose dehydrogenase; carbonyl reductase / ethanol; water / 30 - 50 °C / pH 6.9 - 7.2 / Enzymatic reaction
View Scheme
tert-butyl (6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidin-5-yl]-3-hydroxy-5-oxohept-6-enoate

tert-butyl (6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidin-5-yl]-3-hydroxy-5-oxohept-6-enoate

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide / water; dichloromethane / 5 - 10 °C
2: sodium carbonate; D-Glucose; NADP; glucose dehydrogenase; carbonyl reductase / ethanol; water / 30 - 50 °C / pH 6.9 - 7.2 / Enzymatic reaction
View Scheme
(3R,5S)-6-<(methylsulfonyl)oxy>-3,5-O-isopropylidene-3,5-dihydroxyhexanoic acid tert-butyl ester
135054-68-1

(3R,5S)-6-<(methylsulfonyl)oxy>-3,5-O-isopropylidene-3,5-dihydroxyhexanoic acid tert-butyl ester

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N,N-dimethyl-formamide / 25 - 130 °C
2: hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / isopropyl alcohol
3: sodium hydride / tetrahydrofuran / 0 - 35 °C
4: hydrogenchloride / water; acetonitrile / 35 - 40 °C
View Scheme
[(4R,6S)-2,2-dimethyl-6-(1-phenyl-1H-tetrazol-5-ylsulfanylmethyl)[1,3]dioxan-4-yl]acetic acid tert-butyl ester
380460-39-9

[(4R,6S)-2,2-dimethyl-6-(1-phenyl-1H-tetrazol-5-ylsulfanylmethyl)[1,3]dioxan-4-yl]acetic acid tert-butyl ester

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / isopropyl alcohol
2: sodium hydride / tetrahydrofuran / 0 - 35 °C
3: hydrogenchloride / water; acetonitrile / 35 - 40 °C
View Scheme
[(4R,6S)-2,2-dimethyl-6-(1-phenyl-1H-tetrazole-5-sulfonylmethyl)[1,3]dioxan-4-yl]acetic acid tert-butyl ester
380460-37-7

[(4R,6S)-2,2-dimethyl-6-(1-phenyl-1H-tetrazole-5-sulfonylmethyl)[1,3]dioxan-4-yl]acetic acid tert-butyl ester

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydride / tetrahydrofuran / 0 - 35 °C
2: hydrogenchloride / water; acetonitrile / 35 - 40 °C
View Scheme
N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
147118-37-4

N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydride / tetrahydrofuran / 0 - 35 °C
2: hydrogenchloride / water; acetonitrile / 35 - 40 °C
View Scheme
[4-(4-fluorophenyl)-6-isopropyl-2-(methanesulfonyl(methyl)amino)pyrimidin-5-yl-methyl]triphenylphosphonium triflate

[4-(4-fluorophenyl)-6-isopropyl-2-(methanesulfonyl(methyl)amino)pyrimidin-5-yl-methyl]triphenylphosphonium triflate

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydride / tetrahydrofuran / -15 - 0 °C
2: hydrogenchloride / water; acetonitrile / 35 - 40 °C
View Scheme
rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

rosuvastatin sodium

rosuvastatin sodium

Conditions
ConditionsYield
With sodium hydroxide; water In tetrahydrofuran at 30 - 50℃; for 1 - 2h; Product distribution / selectivity;100%
With water; sodium hydroxide In acetonitrile at 20℃; for 7h; Temperature;97%
With sodium hydroxide In ethanol at 0 - 20℃; for 1h;92%
rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

(E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(methyl(methylsulfonyl)amino)pyrimidin-5-yl)-(3R,5S)-3,5-dihydroxyhept-6-enoic acid, calcium salt

(E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(methyl(methylsulfonyl)amino)pyrimidin-5-yl)-(3R,5S)-3,5-dihydroxyhept-6-enoic acid, calcium salt

Conditions
ConditionsYield
Stage #1: rosuvastatin tert-butyl ester With sodium hydroxide In ethanol; water at 20℃; for 1h;
Stage #2: With calcium chloride In ethanol; water at 0 - 20℃;		94%
Stage #1: rosuvastatin tert-butyl ester With lithium hydroxide In ethanol at 60℃; for 8h;
Stage #2: With calcium chloride In water for 0.5h;		90%
Stage #1: rosuvastatin tert-butyl ester With water; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 50℃; for 2h;
Stage #2: With calcium chloride In water at 0℃; for 0.25h; Product distribution / selectivity;
Stage #1: rosuvastatin tert-butyl ester With water; isopropylamine In tetrahydrofuran at 95 - 100℃; for 2h;
Stage #2: With calcium hydroxide In water at 20℃; for 1h; Product distribution / selectivity;
sodium hydroxide
1310-73-2

sodium hydroxide

rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

rosuvastatin sodium

rosuvastatin sodium

Conditions
ConditionsYield
With ethanol; water at 20 - 60℃; for 4.5h; Product distribution / selectivity;91%
rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

rac-methylbenzylamine
618-36-0

rac-methylbenzylamine

C30H37FN4O5S

C30H37FN4O5S

Conditions
ConditionsYield
In toluene at 100 - 110℃; for 12h;91%
rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

diisobutylamine
110-96-3

diisobutylamine

rosuvastatin diisobutylamine salt

rosuvastatin diisobutylamine salt

Conditions
ConditionsYield
Stage #1: rosuvastatin tert-butyl ester With sodium hydroxide In tetrahydrofuran; water at 5 - 10℃; for 5h;
Stage #2: With citric acid In dichloromethane; water at 5 - 20℃; for 0.5h;
Stage #3: diisobutylamine In acetonitrile at 45 - 50℃; for 0.5h;		90%
rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

tert-butylamine
75-64-9

tert-butylamine

(3R,5S,6E)-7-[4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid-2-methylpropan-2-amine
917805-74-4

(3R,5S,6E)-7-[4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid-2-methylpropan-2-amine

Conditions
ConditionsYield
In water; acetonitrile at 25 - 80℃; Product distribution / selectivity;85%
With water at 95 - 100℃; for 2 - 4h; Product distribution / selectivity;
Stage #1: rosuvastatin tert-butyl ester With sodium hydroxide In water; acetonitrile at 17 - 22℃; for 3h;
Stage #2: tert-butylamine In dichloromethane for 1h; Temperature; Solvent; Reflux;		9.3 g
rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

crestor

crestor

Conditions
ConditionsYield
Stage #1: rosuvastatin tert-butyl ester With sodium hydroxide In methanol; water at 0 - 10℃; for 5h;
Stage #2: With calcium chloride In water at 10 - 15℃;		83.5%
Stage #1: rosuvastatin tert-butyl ester With water; sodium hydroxide at 40 - 45℃; Inert atmosphere;
Stage #2: With calcium chloride at 15 - 20℃; Micron filter;		38%
Stage #1: rosuvastatin tert-butyl ester With sodium hydroxide; water In acetonitrile at 20℃; for 2h;
Stage #2: With calcium chloride In water at 20℃; for 15h; Product distribution / selectivity;
rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

(+)-(3R)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-3-hydroxy-5-oxo-(6E)-heptenoic acid tert-butyl ester

(+)-(3R)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-3-hydroxy-5-oxo-(6E)-heptenoic acid tert-butyl ester

Conditions
ConditionsYield
With manganese(IV) oxide In dichloromethane at 40℃; for 18h; Temperature;80%
With manganese(IV) oxide for 20h; Reflux;17.6 g
rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

rosuvastatin
287714-41-4

rosuvastatin

Conditions
ConditionsYield
With sodium hydroxide; ethanol; water at 20℃; for 2h; Product distribution / selectivity;
Stage #1: rosuvastatin tert-butyl ester With sodium hydroxide; water In tetrahydrofuran at 50 - 55℃; for 1h;
Stage #2: With phosphoric acid; water Product distribution / selectivity;
Stage #1: rosuvastatin tert-butyl ester With sodium hydroxide; water In tetrahydrofuran at 30℃; for 2h;
Stage #2: With hydrogenchloride; water at 20℃; Product distribution / selectivity;
rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

diethylamine
109-89-7

diethylamine

C4H11N*C22H28FN3O6S
917805-73-3

C4H11N*C22H28FN3O6S

Conditions
ConditionsYield
With water at 95 - 100℃; for 3.5h;
rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

N-methylpropan-2-amine
4747-21-1

N-methylpropan-2-amine

C4H11N*C22H28FN3O6S
917805-72-2

C4H11N*C22H28FN3O6S

Conditions
ConditionsYield
With water at 95 - 100℃; for 2h;
rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

tetramethyl ammoniumhydroxide
75-59-2

tetramethyl ammoniumhydroxide

rosuvastatin tetramethyl ammonium salt
917805-79-9

rosuvastatin tetramethyl ammonium salt

Conditions
ConditionsYield
With water at 40 - 45℃; for 1h;
rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

diisopropylamine
108-18-9

diisopropylamine

E-7-[2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-yl]-(3R,5S)-3,5-dihydroxyhept-6-enoic acid diisopropylamine salt
862994-56-7

E-7-[2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-yl]-(3R,5S)-3,5-dihydroxyhept-6-enoic acid diisopropylamine salt

Conditions
ConditionsYield
With water at 95 - 100℃; for 3h;
rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

isopropylamine
75-31-0

isopropylamine

(3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidine-5-yl]-3,5-dihydroxyhept-6-enoic acid isopropylamine
852820-97-4

(3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidine-5-yl]-3,5-dihydroxyhept-6-enoic acid isopropylamine

Conditions
ConditionsYield
With water at 95 - 100℃; for 2 - 3h; Product distribution / selectivity;
In water at 98 - 100℃; for 2h;
rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

SEC-BUTYLAMINE
33966-50-6

SEC-BUTYLAMINE

(E)-7-{4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]-pyrimidin-5-yl}-(3R,5S)-3,5-dihydroxy-hept-6-enoic acid sec-butylammonium salt
917805-75-5

(E)-7-{4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]-pyrimidin-5-yl}-(3R,5S)-3,5-dihydroxy-hept-6-enoic acid sec-butylammonium salt

Conditions
ConditionsYield
With water at 95 - 100℃; for 4h;
rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

Rosuvastatin lactone
503610-43-3

Rosuvastatin lactone

Conditions
ConditionsYield
Stage #1: rosuvastatin tert-butyl ester With potassium hydroxide; water In tetrahydrofuran at 40 - 45℃; for 1.5h;
Stage #2: With phosphoric acid; water In ethyl acetate for 0.333333h; Heating / reflux;
Stage #3: With sodium hydrogencarbonate In water; ethyl acetate
rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

rosuvastatin triol t-butyl ester
1058749-22-6

rosuvastatin triol t-butyl ester

Conditions
ConditionsYield
Stage #1: rosuvastatin tert-butyl ester With boron dimethyl-trifluoro sulphide In tetrahydrofuran at 20℃; for 3h;
Stage #2: With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran; water at 50℃; for 0.5h;
rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

rosuvastatin triol t-butyl ester
1058749-22-6

rosuvastatin triol t-butyl ester

A

rosuvastatin triol calcium

rosuvastatin triol calcium

B

crestor

crestor

Conditions
ConditionsYield
Stage #1: rosuvastatin tert-butyl ester; rosuvastatin triol t-butyl ester With sodium hydroxide; water In ethanol at 20℃; for 2h;
Stage #2: With calcium chloride In water at 20 - 40℃; for 1h;
...Expand
rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

N,N'-dibenzylethylenediamine diacetate
122-75-8

N,N'-dibenzylethylenediamine diacetate

N,N'-dibenzylethylenediamine rosuvastatin
1045601-12-4

N,N'-dibenzylethylenediamine rosuvastatin

Conditions
ConditionsYield
Stage #1: rosuvastatin tert-butyl ester With sodium hydroxide In ethanol; water at 25 - 30℃; for 1h;
Stage #2: N,N'-dibenzylethylenediamine diacetate In water for 2h;
rosuvastatin tert-butyl ester
355806-00-7

rosuvastatin tert-butyl ester

N,N'-dibenzylethylenediamine diacetate
122-75-8

N,N'-dibenzylethylenediamine diacetate

(3R,5S,6E)-7-[4-(4-fluorophenyl)-6-(1-methylethyl)]-2-[methyl(methylsulfonyl)amino-5-pyrimidinyl]-3,5-dihydroxy-6-heptenoic acid N,N'-dibenzylethylenediamine

(3R,5S,6E)-7-[4-(4-fluorophenyl)-6-(1-methylethyl)]-2-[methyl(methylsulfonyl)amino-5-pyrimidinyl]-3,5-dihydroxy-6-heptenoic acid N,N'-dibenzylethylenediamine

Conditions
ConditionsYield
Stage #1: rosuvastatin tert-butyl ester With sodium hydroxide; ethanol; water at 25 - 30℃; for 1h;
Stage #2: N,N'-dibenzylethylenediamine diacetate In water for 2h; Product distribution / selectivity;

tert-Butyl rosuvastatin Chemical Properties

Molecular structure of tert-Butyl rosuvastatin (CAS NO.355806-00-7) is:

Product Name: tert-Butyl rosuvastatin
CAS Registry Number: 355806-00-7
Systematic Name: tert-butyl (3R,5S,6E)-7-{4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl}-3,5-dihydroxyhept-6-enoate 
Empirical Formula: C26H36FN3O6S
Molecular Weight: 537.6439
Molar Volume: 426.796 cm3
Surface Tension: 51.909 dyne/cm
Density: 1.26 g/cm3
Flash Point: 379.661 °C
Enthalpy of Vaporization: 108.192 kJ/mol
Boiling Point: 704.158 °C at 760 mmHg
Product Categories: Rosuvastatin Calcium and its intermediates

tert-Butyl rosuvastatin Specification

 tert-Butyl rosuvastatin , its cas register number is 355806-00-7. It also can be called tert-Butyl (6E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl]-(3R,5S)-3,5-dihydroxyhept-6-enoate ; (3R,5S,6E)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-[(methanesulfonyl)methylamino]pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid tert-butyl ester .It is a white to off-white crystal powder.

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