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355806-00-7

Basic Information
CAS No.: 355806-00-7
Name: tert-Butyl rosuvastatin
Article Data: 29
Molecular Structure:
Molecular Structure of 355806-00-7 (tert-Butyl rosuvastatin)
Formula: C26H36FN3O6S
Molecular Weight: 537.653
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)-;
EINECS: 609-144-4
Density: 1.26 g/cm3
Boiling Point: 704.158 °C at 760 mmHg
Flash Point: 379.661 °C
Appearance: white to off-white crystal powder
PSA: 138.30000
LogP: 4.73960
Synthetic route
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

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%
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

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

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

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

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

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%
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

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%
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

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
1054627-26-7

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

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
141942-89-4

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

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
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Chemistry

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

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.