Product Name

  • Name

    Lovastatin

  • EINECS 616-212-7
  • CAS No. 75330-75-5
  • Article Data18
  • CAS DataBase
  • Density 1.12 g/cm3
  • Solubility 0.0004 mg/mL at 25 °C in water
  • Melting Point 175 °C
  • Formula C24H36O5
  • Boiling Point 559.2 °C at 760 mmHg
  • Molecular Weight 404.547
  • Flash Point 185.3 °C
  • Transport Information UN 3077
  • Appearance White solid
  • Safety 22-24/25-36/37/39-26
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 75330-75-5 (Lovastatin)
  • Hazard Symbols IrritantXi
  • Synonyms MK-803;Belvas;(1S-(1alpha(R),3alpha,7beta,8beta(2S,4S),8abeta))-(1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthyl) 2-methylbutanoate;Rodatin;Paschol;Artein;Butanoic acid, 2-methyl-, 1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(tetrahydro-4-hydroxy-6-- oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (1S-(1alpha(R*),3alpha,7beta,8beta(2S*,4S*),8abeta))-;Sivlor;MK 803;Mevinolin;Prestwick_819;Antibiotic MB 530B;Lestatin;Colevix;Lovastation;Mevinacor;Lovasterol;[(1S,3R,7R,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxo-oxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate;2-Methyl-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenyl ester butanoic acid;Hipolip;Tecnolip;Lovastatine [French];6-alpha-Methylcompactin;MSD 803;Cholestra;Lovastatin (USP);ML-530B;Monacolin K;Hipovastin;Taucor;Mevacor (TN);[(1S,3R,7R,8S,8aR)-8-[2-[(4R)-4-hydroxy-6-oxo-oxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate;Teroltrat;Lozutin;Lipofren;Lipdip;
  • PSA 72.83000
  • LogP 4.19550

Synthetic route

6(R)-<2-<1,2,6,7,8,8a(R)-Hexahydro-2(S),6(R)-dimethyl-8(S)-<<2(S)-methylbutyryl>oxy>-1(S)-naphtyl>ethyl>-3,4,5,6-tetrahydro-4(R)-<(tert-butyldimethylsilyl)oxy>-2H-pyran-2-one
79691-11-5

6(R)-<2-<1,2,6,7,8,8a(R)-Hexahydro-2(S),6(R)-dimethyl-8(S)-<<2(S)-methylbutyryl>oxy>-1(S)-naphtyl>ethyl>-3,4,5,6-tetrahydro-4(R)-<(tert-butyldimethylsilyl)oxy>-2H-pyran-2-one

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
With hydrogen fluoride In acetonitrile at 25℃; for 1.4h;94%
With hydrogen fluoride In acetonitrile at 0℃; for 5h;77%
With tetrabutyl ammonium fluoride; acetic acid In tetrahydrofuran
With tetrabutyl ammonium fluoride; acetic acid In tetrahydrofuran for 18h; Ambient temperature;
ammonium mevinolinic acid

ammonium mevinolinic acid

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Stage #1: ammonium mevinolinic acid With phosphoric acid In toluene; butanone at 20 - 82℃; for 2 - 2.5h;
Stage #2: With triethylamine In water; toluene; butanone at 20℃;		78.2%
With sulfuric acid In acetonitrile at -22 - -17℃; for 0.5h;
117020-90-3, 117066-28-1

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
With Celite; silver carbonate In toluene at 85 - 95℃; for 1h;77%
With Celite; toluene; silver carbonate In toluene at 90℃; for 1h;77%
lovastatin acid
75225-51-3, 137767-34-1

lovastatin acid

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
With phosphoric acid In water; toluene at 20 - 55℃; for 19h; pH=3.5; Product distribution / selectivity;76.12%
With trifluoroacetic acid In ethyl acetate for 0.166667h;
(S)-2-Methyl-butyric acid (1S,3S,7R,8R,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-3,7-dimethyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester
85614-12-6

(S)-2-Methyl-butyric acid (1S,3S,7R,8R,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-3,7-dimethyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C
2: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C
3: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C
View Scheme
(S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-4-chloro-6-formyloxy-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester
153079-18-6

(S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-4-chloro-6-formyloxy-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: imidazole / acetonitrile / 25 °C
2: Ti(OiPr)4 / propan-2-ol / 0.5 h / 60 °C
3: 92 percent / PDC / toluene / 0.33 h / 80 °C
4: 78 percent / AgOTf/2,6-di-tert-butyl-4-methylpyridine / 24 h / 25 °C
5: 65 percent / tetrahydrofuran / -78 °C
6: H+ / CHCl3
7: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C
8: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C
9: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C
View Scheme
2-methyl-butyric acid 8-{2-[4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-6-oxo-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl ester
153079-17-5

2-methyl-butyric acid 8-{2-[4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-6-oxo-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl ester

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 65 percent / tetrahydrofuran / -78 °C
2: H+ / CHCl3
3: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C
4: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C
5: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C
View Scheme
(S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-4-chloro-6-hydroxy-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester
153079-20-0

(S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-4-chloro-6-hydroxy-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 92 percent / PDC / toluene / 0.33 h / 80 °C
2: 78 percent / AgOTf/2,6-di-tert-butyl-4-methylpyridine / 24 h / 25 °C
3: 65 percent / tetrahydrofuran / -78 °C
4: H+ / CHCl3
5: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C
6: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C
7: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C
View Scheme
(S)-2-Methyl-butyric acid (1S,3R,7R,8R,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-3,7-dimethyl-6-oxo-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-yl ester
153079-22-2

(S)-2-Methyl-butyric acid (1S,3R,7R,8R,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-3,7-dimethyl-6-oxo-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-yl ester

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: H+ / CHCl3
2: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C
3: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C
4: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C
View Scheme
(S)-2-Methyl-butyric acid (1S,4S,7R,8R,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-4-chloro-7-methyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester
153079-21-1

(S)-2-Methyl-butyric acid (1S,4S,7R,8R,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-4-chloro-7-methyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 78 percent / AgOTf/2,6-di-tert-butyl-4-methylpyridine / 24 h / 25 °C
2: 65 percent / tetrahydrofuran / -78 °C
3: H+ / CHCl3
4: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C
5: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C
6: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C
View Scheme
(S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-4-chloro-6-formyloxy-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester
153079-19-7

(S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-4-chloro-6-formyloxy-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: Ti(OiPr)4 / propan-2-ol / 0.5 h / 60 °C
2: 92 percent / PDC / toluene / 0.33 h / 80 °C
3: 78 percent / AgOTf/2,6-di-tert-butyl-4-methylpyridine / 24 h / 25 °C
4: 65 percent / tetrahydrofuran / -78 °C
5: H+ / CHCl3
6: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C
7: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C
8: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C
View Scheme
(S)-2-Methyl-butyric acid (1S,3R,7R,8R,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-3,7-dimethyl-6-trifluoromethanesulfonyloxy-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
153079-24-4

(S)-2-Methyl-butyric acid (1S,3R,7R,8R,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-3,7-dimethyl-6-trifluoromethanesulfonyloxy-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C
2: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C
View Scheme
<1S-<1α(R*),3α,7β,8β(4S*,6R*),8aβ>>-1,2,3,7,8,8a-hexahydro-8-<2-<6-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-3,7-dimethyl-1-naphthalenyl 2-methylbutanoate
116996-47-5

<1S-<1α(R*),3α,7β,8β(4S*,6R*),8aβ>>-1,2,3,7,8,8a-hexahydro-8-<2-<6-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-3,7-dimethyl-1-naphthalenyl 2-methylbutanoate

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) (COCl)2; 2.) Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 20 min
2: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
3: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
Multi-step reaction with 3 steps
1: 97 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
2: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
3: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 95 °C
View Scheme
<1S-<1α(R*),3α,7β,8β(4S*,6R*),8aβ>>-8-<2-<2,2-dimethyl-6-(2-oxoethyl)-1,3-dioxan-4-yl>ethyl>-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-1-naphthalenyl 2-methylbutanoate
116996-48-6

<1S-<1α(R*),3α,7β,8β(4S*,6R*),8aβ>>-8-<2-<2,2-dimethyl-6-(2-oxoethyl)-1,3-dioxan-4-yl>ethyl>-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-1-naphthalenyl 2-methylbutanoate

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
2: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
Multi-step reaction with 2 steps
1: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
2: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 95 °C
View Scheme
<4R-<4α*(1R*,2S*)>6α>>-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-α-(2-methyl-5-oxo-3-cyclohexen-1-yl)-1,3-dioxane-4-propanal
116996-31-7, 126060-10-4

<4R-<4α*(1R*,2S*)>6α>>-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-α-(2-methyl-5-oxo-3-cyclohexen-1-yl)-1,3-dioxane-4-propanal

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 50 percent / (Ph3P)3RhCl / toluene; acetonitrile / 2.5 h / Heating
2: 1.) LDA / 1.)Et2O, -78 deg C, 45 min; 2.) -78 deg C, 10 min
3: 85 percent / i-Pr2NH / DMAP / diethyl ether / 24 h / Ambient temperature
4: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C -> r.t., 3 h
5: 86 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 4 h
6: 1.) Bu4NF ; 2.) t-BuPh2SiCl, Et3N / 2.) DMAP / 1.) THF, r.t., 22 h; 2.) CH2Cl2, r.t., 24 h
7: 97 percent / Et3N / DMAP / CH2Cl2 / 88 h / Ambient temperature
8: 95 percent / Bu4NF / tetrahydrofuran / 3 h / Ambient temperature
9: 1.) (COCl)2; 2.) Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 20 min
10: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
11: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
Multi-step reaction with 12 steps
1: 50 percent / (Ph3P)3RhCl / toluene; benzonitrile / 2.5 h / Heating
2: 1.) lithium diisopropylamide (LDA) / 1.) ether, -78 deg C, 45 min, 2.) -78 deg C, 10 min
3: 85 percent / diisopropylamine, 4-(dimethylamino)pyridine (DMAP) / diethyl ether / 24 h / Ambient temperature
4: 85 percent / 1.) O3, 2.) triphenylphosphine / CH2Cl2 / 1.) -78 deg C, 5 min, 2.) 3 h
5: 86 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 4 h
6: 99 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 22 h / Ambient temperature
7: Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 24 h / Ambient temperature
8: 91 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 72 h / Ambient temperature
9: 95 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 3 h / Ambient temperature
10: 97 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
11: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
12: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 95 °C
View Scheme
<1S-<1α,3α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenol
116996-45-3

<1S-<1α,3α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenol

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 97 percent / Et3N / DMAP / CH2Cl2 / 88 h / Ambient temperature
2: 95 percent / Bu4NF / tetrahydrofuran / 3 h / Ambient temperature
3: 1.) (COCl)2; 2.) Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 20 min
4: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
5: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
Multi-step reaction with 5 steps
1: 91 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 72 h / Ambient temperature
2: 95 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 3 h / Ambient temperature
3: 97 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
4: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
5: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 95 °C
View Scheme
<4S-<4α,5α(4S*,4S*),6β(1R*,3S*)>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-6-(1-hydroxy-3-methyl-4-pentenyl)-4-methyl-2-cyclohexen-1-one
117020-88-9

<4S-<4α,5α(4S*,4S*),6β(1R*,3S*)>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-6-(1-hydroxy-3-methyl-4-pentenyl)-4-methyl-2-cyclohexen-1-one

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 85 percent / i-Pr2NH / DMAP / diethyl ether / 24 h / Ambient temperature
2: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C -> r.t., 3 h
3: 86 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 4 h
4: 1.) Bu4NF ; 2.) t-BuPh2SiCl, Et3N / 2.) DMAP / 1.) THF, r.t., 22 h; 2.) CH2Cl2, r.t., 24 h
5: 97 percent / Et3N / DMAP / CH2Cl2 / 88 h / Ambient temperature
6: 95 percent / Bu4NF / tetrahydrofuran / 3 h / Ambient temperature
7: 1.) (COCl)2; 2.) Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 20 min
8: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
9: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
Multi-step reaction with 10 steps
1: 85 percent / diisopropylamine, 4-(dimethylamino)pyridine (DMAP) / diethyl ether / 24 h / Ambient temperature
2: 85 percent / 1.) O3, 2.) triphenylphosphine / CH2Cl2 / 1.) -78 deg C, 5 min, 2.) 3 h
3: 86 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 4 h
4: 99 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 22 h / Ambient temperature
5: Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 24 h / Ambient temperature
6: 91 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 72 h / Ambient temperature
7: 95 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 3 h / Ambient temperature
8: 97 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
9: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
10: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 95 °C
View Scheme
<1S-<1α,3α,7β,8β(4Σ*,6R*)8aβ>>-<<8-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenyl>oxy>triethylsilane
116996-44-2

<1S-<1α,3α,7β,8β(4Σ*,6R*)8aβ>>-<<8-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenyl>oxy>triethylsilane

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) Bu4NF ; 2.) t-BuPh2SiCl, Et3N / 2.) DMAP / 1.) THF, r.t., 22 h; 2.) CH2Cl2, r.t., 24 h
2: 97 percent / Et3N / DMAP / CH2Cl2 / 88 h / Ambient temperature
3: 95 percent / Bu4NF / tetrahydrofuran / 3 h / Ambient temperature
4: 1.) (COCl)2; 2.) Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 20 min
5: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
6: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
Multi-step reaction with 7 steps
1: 99 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 22 h / Ambient temperature
2: Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 24 h / Ambient temperature
3: 91 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 72 h / Ambient temperature
4: 95 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 3 h / Ambient temperature
5: 97 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
6: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
7: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 95 °C
View Scheme
<1S-<1α(R*),3α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenyl 2-methylbutanoate
116996-46-4

<1S-<1α(R*),3α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenyl 2-methylbutanoate

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 95 percent / Bu4NF / tetrahydrofuran / 3 h / Ambient temperature
2: 1.) (COCl)2; 2.) Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 20 min
3: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
4: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
Multi-step reaction with 4 steps
1: 95 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 3 h / Ambient temperature
2: 97 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
3: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
4: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 95 °C
View Scheme
<4S-<4α,5α(4S*,6R*),6β(1R*,3S*)>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-6-<3-methyl-1-<(triethylsilyl)oxy>-4-pentenyl>-2-cyclohexen-1-one
117020-89-0

<4S-<4α,5α(4S*,6R*),6β(1R*,3S*)>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-6-<3-methyl-1-<(triethylsilyl)oxy>-4-pentenyl>-2-cyclohexen-1-one

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C -> r.t., 3 h
2: 86 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 4 h
3: 1.) Bu4NF ; 2.) t-BuPh2SiCl, Et3N / 2.) DMAP / 1.) THF, r.t., 22 h; 2.) CH2Cl2, r.t., 24 h
4: 97 percent / Et3N / DMAP / CH2Cl2 / 88 h / Ambient temperature
5: 95 percent / Bu4NF / tetrahydrofuran / 3 h / Ambient temperature
6: 1.) (COCl)2; 2.) Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 20 min
7: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
8: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
Multi-step reaction with 9 steps
1: 85 percent / 1.) O3, 2.) triphenylphosphine / CH2Cl2 / 1.) -78 deg C, 5 min, 2.) 3 h
2: 86 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 4 h
3: 99 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 22 h / Ambient temperature
4: Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 24 h / Ambient temperature
5: 91 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 72 h / Ambient temperature
6: 95 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 3 h / Ambient temperature
7: 97 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
8: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
9: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 95 °C
View Scheme
<1S-<1α(αS,γR*),5β,6β(4Σ*,6R*)>>-6-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-α,5-dimethyl-2-oxo-γ-<(triethylsilyl)oxy>-3-cyclohexene-1-butanal
116996-43-1

<1S-<1α(αS,γR*),5β,6β(4Σ*,6R*)>>-6-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-α,5-dimethyl-2-oxo-γ-<(triethylsilyl)oxy>-3-cyclohexene-1-butanal

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 86 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 4 h
2: 1.) Bu4NF ; 2.) t-BuPh2SiCl, Et3N / 2.) DMAP / 1.) THF, r.t., 22 h; 2.) CH2Cl2, r.t., 24 h
3: 97 percent / Et3N / DMAP / CH2Cl2 / 88 h / Ambient temperature
4: 95 percent / Bu4NF / tetrahydrofuran / 3 h / Ambient temperature
5: 1.) (COCl)2; 2.) Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 20 min
6: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
7: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
Multi-step reaction with 8 steps
1: 86 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 4 h
2: 99 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 22 h / Ambient temperature
3: Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 24 h / Ambient temperature
4: 91 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 72 h / Ambient temperature
5: 95 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 3 h / Ambient temperature
6: 97 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
7: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
8: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 95 °C
View Scheme
<4R-<4α(4R*,5R*),6α>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-one
116996-32-8

<4R-<4α(4R*,5R*),6α>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-one

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 1.) LDA / 1.)Et2O, -78 deg C, 45 min; 2.) -78 deg C, 10 min
2: 85 percent / i-Pr2NH / DMAP / diethyl ether / 24 h / Ambient temperature
3: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C -> r.t., 3 h
4: 86 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 4 h
5: 1.) Bu4NF ; 2.) t-BuPh2SiCl, Et3N / 2.) DMAP / 1.) THF, r.t., 22 h; 2.) CH2Cl2, r.t., 24 h
6: 97 percent / Et3N / DMAP / CH2Cl2 / 88 h / Ambient temperature
7: 95 percent / Bu4NF / tetrahydrofuran / 3 h / Ambient temperature
8: 1.) (COCl)2; 2.) Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 20 min
9: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
10: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
Multi-step reaction with 11 steps
1: 1.) lithium diisopropylamide (LDA) / 1.) ether, -78 deg C, 45 min, 2.) -78 deg C, 10 min
2: 85 percent / diisopropylamine, 4-(dimethylamino)pyridine (DMAP) / diethyl ether / 24 h / Ambient temperature
3: 85 percent / 1.) O3, 2.) triphenylphosphine / CH2Cl2 / 1.) -78 deg C, 5 min, 2.) 3 h
4: 86 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 4 h
5: 99 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 22 h / Ambient temperature
6: Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 24 h / Ambient temperature
7: 91 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 72 h / Ambient temperature
8: 95 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 3 h / Ambient temperature
9: 97 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
10: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
11: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 95 °C
View Scheme
(S)-2-methylbutyric anhydride
84131-91-9

(S)-2-methylbutyric anhydride

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 97 percent / Et3N / DMAP / CH2Cl2 / 88 h / Ambient temperature
2: 95 percent / Bu4NF / tetrahydrofuran / 3 h / Ambient temperature
3: 1.) (COCl)2; 2.) Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 20 min
4: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
5: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
(S)-2-methylbutanoyl chloride
27763-54-8

(S)-2-methylbutanoyl chloride

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 4-(dimethylamino)pyridine (DMAP), pyridine / 1.) 0 deg C, 1 h, 2.) RT, 18 h
2: acetic acid, Bu4NF*3H2O / tetrahydrofuran / 18 h / Ambient temperature
View Scheme
(4R,6R)-6-[2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthyl)ethyl]-4-[(tert-butyldimethylsilyl)oxy]-3,4,5,6-tetrahydro-2H-pyran-2-one
79902-31-1

(4R,6R)-6-[2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthyl)ethyl]-4-[(tert-butyldimethylsilyl)oxy]-3,4,5,6-tetrahydro-2H-pyran-2-one

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 4-(dimethylamino)pyridine (DMAP), pyridine / 1.) 0 deg C, 1 h, 2.) RT, 18 h
2: acetic acid, Bu4NF*3H2O / tetrahydrofuran / 18 h / Ambient temperature
View Scheme
(1S,3R,7S,8S,8aR)-8-{2-[(4R,6S)-6-(2-Hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-ol
125975-03-3

(1S,3R,7S,8S,8aR)-8-{2-[(4R,6S)-6-(2-Hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-ol

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 24 h / Ambient temperature
2: 91 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 72 h / Ambient temperature
3: 95 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 3 h / Ambient temperature
4: 97 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
5: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
6: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 95 °C
View Scheme
lovastatin
75330-75-5

lovastatin

α,β-dehydrolovastatin
109273-98-5

α,β-dehydrolovastatin

Conditions
ConditionsYield
With methanesulfonyl chloride; triethylamine In dichloromethane at 20℃; for 1h;100%
With dmap; methanesulfonyl chloride In acetonitrile at 20℃;90%
With Burgess Reagent In benzene at 60℃; for 1.5h;61%
With methanesulfonyl chloride; triethylamine In dichloromethane at 20℃; for 1h;460 mg
lovastatin
75330-75-5

lovastatin

N-butylamine
109-73-9

N-butylamine

N-butyl-7-<1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-<<2(S)-methylbutanoyl>oxy>-1(S)-naphthyl>-3(R),5(R)-dihydroxyheptanoic acid amide
134970-29-9

N-butyl-7-<1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-<<2(S)-methylbutanoyl>oxy>-1(S)-naphthyl>-3(R),5(R)-dihydroxyheptanoic acid amide

Conditions
ConditionsYield
at 80℃; for 1h;100%
Heating / reflux;
Reflux;
at 70℃; for 3h; Inert atmosphere;
lovastatin
75330-75-5

lovastatin

Cyclopropylamine
765-30-0

Cyclopropylamine

N-cyclopropyl-7-[1,2,6,7,8,8a(R)-hexahydro-2(s),6(R)-dimethyl-8(s)-[[2(S)-methylbutanoyl]oxy]-1(S)-naphthyl]-3(R),5(R)-dihydroxyheptanoic acid amide

N-cyclopropyl-7-[1,2,6,7,8,8a(R)-hexahydro-2(s),6(R)-dimethyl-8(s)-[[2(S)-methylbutanoyl]oxy]-1(S)-naphthyl]-3(R),5(R)-dihydroxyheptanoic acid amide

Conditions
ConditionsYield
at 40 - 42℃; for 8h; Inert atmosphere;100%
lovastatin
75330-75-5

lovastatin

monacolin J hydroxy acid
132748-10-8

monacolin J hydroxy acid

Conditions
ConditionsYield
With potassium hydroxide In methanol at 20℃; Reflux;98%
Stage #1: lovastatin; potassium hydroxide In ethanol; water at 20℃; for 12.5 - 17h; Heating / reflux;
Stage #2: With hydrogenchloride; water In diethyl ether at 5 - 10℃; for 1h; pH=5;		93%
Stage #1: lovastatin With potassium hydroxide In water; isopropyl alcohol at 80℃; for 7h;
Stage #2: With hydrogenchloride In water at 12 - 17℃; for 2h; pH=3 - 4; Cooling with ice;		90%
lovastatin
75330-75-5

lovastatin

triethylamine
121-44-8

triethylamine

(3R,5S)-7-[(1S,2S,6R,8S,8aR)-2,6-Dimethyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-3,5-dihydroxy-heptanoic acid; compound with triethyl-amine

(3R,5S)-7-[(1S,2S,6R,8S,8aR)-2,6-Dimethyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-3,5-dihydroxy-heptanoic acid; compound with triethyl-amine

Conditions
ConditionsYield
Stage #1: lovastatin With sodium hydroxide In methanol; water at 20℃; for 2h;
Stage #2: triethylamine In ethyl acetate at 20℃; for 4h;		98%
lovastatin
75330-75-5

lovastatin

(1S,3R,7S,8S,8aR)-8-((3R,5R)-3,5-dihydroxy-7-(hydroxyamino)-7-oxoheptyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (S)-2-methylbutanoate

(1S,3R,7S,8S,8aR)-8-((3R,5R)-3,5-dihydroxy-7-(hydroxyamino)-7-oxoheptyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (S)-2-methylbutanoate

Conditions
ConditionsYield
With hydroxylamine In tetrahydrofuran; water for 72h;98%
With hydroxylamine In tetrahydrofuran; water at 20℃; for 1h;92%
lovastatin
75330-75-5

lovastatin

7-[1',2',6',7',8',8a'(R)-hexahydro-2'(S),6'(R)-dimethyl-8'(S)-hydroxy-1'(S)-naphthyl]-3(R),5 (R)-dihydroxy heptanoic acid

7-[1',2',6',7',8',8a'(R)-hexahydro-2'(S),6'(R)-dimethyl-8'(S)-hydroxy-1'(S)-naphthyl]-3(R),5 (R)-dihydroxy heptanoic acid

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran; water at -30 - 20℃; for 5h;94%
pivaloyl chloride
3282-30-2

pivaloyl chloride

lovastatin
75330-75-5

lovastatin

(2R,4R)-2-[2-((1S,2S,6R,8S,8aR)-1,2,3,7,8,8a-hexahydro-2,6-dimethyl-8-{[(S)-2-methylbutanoyl]oxy}naphthalen-1-yl)ethyl]-3,4,5,6-tetrahydro-6-oxo-2H-pyran-4-yl 2,2-dimethylpropanoate
479482-41-2

(2R,4R)-2-[2-((1S,2S,6R,8S,8aR)-1,2,3,7,8,8a-hexahydro-2,6-dimethyl-8-{[(S)-2-methylbutanoyl]oxy}naphthalen-1-yl)ethyl]-3,4,5,6-tetrahydro-6-oxo-2H-pyran-4-yl 2,2-dimethylpropanoate

Conditions
ConditionsYield
With pyridine In toluene at 20℃;92%
With pyridine In toluene at 20℃; for 24h; Inert atmosphere;77%
benzoyl chloride
98-88-4

benzoyl chloride

lovastatin
75330-75-5

lovastatin

(2R,4R)-2-[2-((1S,2S,6R,8S,8aR)-1,2,3,7,8,8a-hexahydro-2,6-dimethyl-8-{[(S)-2-methylbutanoyl]oxy}naphthalen-1-yl)ethyl]-3,4,5,6-tetrahydro-6-oxo-2H-pyran-4-yl benzoate
81189-93-7

(2R,4R)-2-[2-((1S,2S,6R,8S,8aR)-1,2,3,7,8,8a-hexahydro-2,6-dimethyl-8-{[(S)-2-methylbutanoyl]oxy}naphthalen-1-yl)ethyl]-3,4,5,6-tetrahydro-6-oxo-2H-pyran-4-yl benzoate

Conditions
ConditionsYield
With pyridine In toluene at 20℃; for 18h;91%
With pyridine In toluene at 20℃; for 24h; Inert atmosphere;85%
lovastatin
75330-75-5

lovastatin

6(R)-<2-<1,2,3,5,6,7,8,8a(R)-Octahydro-2(S),6(R)-dimethyl-8(R)-<<2(S)-methylbutyryl>oxy>-1(S)-naphthyl>ethyl>-3,4,5,6-tetrahydro-4(R)-hydroxy-2H-pyran-2-one
79691-09-1

6(R)-<2-<1,2,3,5,6,7,8,8a(R)-Octahydro-2(S),6(R)-dimethyl-8(R)-<<2(S)-methylbutyryl>oxy>-1(S)-naphthyl>ethyl>-3,4,5,6-tetrahydro-4(R)-hydroxy-2H-pyran-2-one

Conditions
ConditionsYield
With (η4-1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) hexafluorophosphate; hydrogen In dichloromethane at 20℃; under 760 Torr; for 1.5h;90%
Multi-step reaction with 2 steps
1: 1.48 g / imidazole / dimethylformamide / 5 h / 35 °C
2: 50 mg / triethylsilane, trifluoroacetic acid / CH2Cl2 / 24 h / Ambient temperature
View Scheme
lovastatin
75330-75-5

lovastatin

7-[1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-hydroxy-1(S)-naphthyl]-3(R),5(R)-dihydroxyheptanoic acid
761354-04-5

7-[1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-hydroxy-1(S)-naphthyl]-3(R),5(R)-dihydroxyheptanoic acid

Conditions
ConditionsYield
Stage #1: lovastatin With potassium hydroxide; ethanol; water In isopropyl alcohol at 20℃; for 6.5h; Heating / reflux;
Stage #2: With hydrogenchloride In water; isopropyl alcohol for 1h; pH=<= 3;		90%
lovastatin
75330-75-5

lovastatin

A

(4R,6R)-4-hydroxy-6-(2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl)tetrahydro-2H-pyran-2-one
151006-15-4, 79952-42-4

(4R,6R)-4-hydroxy-6-(2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl)tetrahydro-2H-pyran-2-one

B

monacolin J hydroxy acid
132748-10-8

monacolin J hydroxy acid

Conditions
ConditionsYield
Stage #1: lovastatin With ammonia; water; enzyme SEQ ID NO:4 (encoded by SEQ ID NO:3) at 40℃; for 18.75 - 27h; pH=9.5; Enzymatic reaction;
Stage #2: In water pH=2.5; Product distribution / selectivity; Acidic aqueous solution;		A n/a
B 89.4%
Stage #1: lovastatin With methanol; sodium hydroxide; water at 20℃;
Stage #2: With hydrogenchloride In methanol; water pH=7 - 8;
Stage #3: With hydrogenchloride; methanol; methanesulfonic acid; ammonia; water; lovastatin esterase SEQ ID NO:4 (encoded by SEQ ID NO:3) Product distribution / selectivity; more than 3 stages;
With water; potassium hydroxide In methanol for 21h; Reflux;
lovastatin
75330-75-5

lovastatin

(4R,6R)-4-hydroxy-6-(2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl)tetrahydro-2H-pyran-2-one
151006-15-4, 79952-42-4

(4R,6R)-4-hydroxy-6-(2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl)tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
Stage #1: lovastatin With water; lithium hydroxide at 100℃;
Stage #2: With hydrogenchloride In water pH=< 2;
Stage #3: With calcium hydride In toluene at 110℃; for 1h;		89%
With lithium hydroxide In tetrahydrofuran; methanol at 66℃; for 2h; Inert atmosphere;73%
With lithium hydroxide for 24h; Heating;
lovastatin
75330-75-5

lovastatin

tert-butylamine
75-64-9

tert-butylamine

lovastatin tert-butylamine salt

lovastatin tert-butylamine salt

Conditions
ConditionsYield
With water at 50 - 55℃; for 3.5h;88%
lovastatin
75330-75-5

lovastatin

(1S,3R,7S,8S,8aR)-3,7-dimethyl-8-((3R,5S)-3,5,7-trihydroxyheptyl)-1,2,3,7,8,8ahexahydronaphthalen-1-yl 2-methylbutanoate
221192-13-8

(1S,3R,7S,8S,8aR)-3,7-dimethyl-8-((3R,5S)-3,5,7-trihydroxyheptyl)-1,2,3,7,8,8ahexahydronaphthalen-1-yl 2-methylbutanoate

Conditions
ConditionsYield
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;87%
lovastatin
75330-75-5

lovastatin

2-naphthaloyl chloride
2243-83-6

2-naphthaloyl chloride

(S)-2-methyl-butyric acid (3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-(2-naphthoyloxy)-6-oxo-tetrahydro-pyran-2yl]-ethyl}-3,7-dimetyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

(S)-2-methyl-butyric acid (3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-(2-naphthoyloxy)-6-oxo-tetrahydro-pyran-2yl]-ethyl}-3,7-dimetyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

Conditions
ConditionsYield
With pyridine In toluene at 20℃; for 24h; Inert atmosphere;86%
lovastatin
75330-75-5

lovastatin

<1S-<1α(3R*,5S*),2α,6β,8β,8aα>>-7-(1,2,6,7,8,8a-Hexahydro-8-hydroxy-2,6-dimethyl-1-naphthalenyl)-1,3,5-heptanetriol
148969-22-6

<1S-<1α(3R*,5S*),2α,6β,8β,8aα>>-7-(1,2,6,7,8,8a-Hexahydro-8-hydroxy-2,6-dimethyl-1-naphthalenyl)-1,3,5-heptanetriol

Conditions
ConditionsYield
With lithium aluminium tetrahydride84%
With lithium aluminium tetrahydride In tetrahydrofuran for 5h;84%
With lithium aluminium tetrahydride In diethyl ether for 3h;80%
acetic anhydride
108-24-7

acetic anhydride

lovastatin
75330-75-5

lovastatin

(S)-2-methyl-butyric acid (3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-acetoxy-6-oxo-tetrahydro-pyran-2yl]-ethyl}-3,7-dimetyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
81189-92-6

(S)-2-methyl-butyric acid (3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-acetoxy-6-oxo-tetrahydro-pyran-2yl]-ethyl}-3,7-dimetyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

Conditions
ConditionsYield
With pyridine at 20℃; for 2.5h; Inert atmosphere;84%
lovastatin
75330-75-5

lovastatin

(1S,3R,7S,8S,8aR)-8-((3R,5R)-7-amino-3,5-dihydroxy-7-oxoheptyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (S)-2-methylbutanoate
118159-61-8

(1S,3R,7S,8S,8aR)-8-((3R,5R)-7-amino-3,5-dihydroxy-7-oxoheptyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (S)-2-methylbutanoate

Conditions
ConditionsYield
With ammonia In methanol at 20℃; for 24h;79%
lovastatin
75330-75-5

lovastatin

(1S,3R,7S,8S,8aR)-7,7-dideuterio-3,7-dimethyl-8-((3R,5S)-3,5,7-trihydroxyheptyl)-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2-methylbutanoate

(1S,3R,7S,8S,8aR)-7,7-dideuterio-3,7-dimethyl-8-((3R,5S)-3,5,7-trihydroxyheptyl)-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2-methylbutanoate

Conditions
ConditionsYield
With samarium diiodide; water-d2 In tetrahydrofuran at 23℃; for 2h; Inert atmosphere; chemoselective reaction;74%
succinic acid anhydride
108-30-5

succinic acid anhydride

lovastatin
75330-75-5

lovastatin

lovastatin succinate monoester

lovastatin succinate monoester

Conditions
ConditionsYield
With pyridine at 50℃; for 48h;72%
lovastatin
75330-75-5

lovastatin

chloroacetyl chloride
79-04-9

chloroacetyl chloride

C26H37ClO6

C26H37ClO6

Conditions
ConditionsYield
With pyridine In toluene at 0 - 20℃; for 18h;70%
4-(trifluoromethoxy)benzoyl chloride
36823-88-8

4-(trifluoromethoxy)benzoyl chloride

lovastatin
75330-75-5

lovastatin

(S)-2-methyl-butyric acid (3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-(4-trifluoromethoxybenzoyloxy)-6-oxo-tetrahydro-pyran-2yl]-ethyl}-3,7-dimetyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

(S)-2-methyl-butyric acid (3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-(4-trifluoromethoxybenzoyloxy)-6-oxo-tetrahydro-pyran-2yl]-ethyl}-3,7-dimetyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

Conditions
ConditionsYield
With pyridine In toluene at 20℃; for 24h; Inert atmosphere;64%
4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

lovastatin
75330-75-5

lovastatin

(S)-2-methyl-butyric acid (3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-(4-chlorobenzoyloxy)-6-oxo-tetrahydro-pyran-2yl]-ethyl}-3,7-dimetyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

(S)-2-methyl-butyric acid (3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-(4-chlorobenzoyloxy)-6-oxo-tetrahydro-pyran-2yl]-ethyl}-3,7-dimetyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

Conditions
ConditionsYield
With pyridine In toluene at 20℃; for 24h; Inert atmosphere;64%
4-(methylsulfinyl)benzoic acid
33963-58-5

4-(methylsulfinyl)benzoic acid

lovastatin
75330-75-5

lovastatin

(2R,4R)-2-(2-((1S,2S,6R,8S,8aR)-2,6-dimethyl-8-(((S)-2-methylbutanoyl)oxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl)-6-oxotetrahydro-2H-pyran-4-yl 4-(methylsulfinyl)benzoate

(2R,4R)-2-(2-((1S,2S,6R,8S,8aR)-2,6-dimethyl-8-(((S)-2-methylbutanoyl)oxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl)-6-oxotetrahydro-2H-pyran-4-yl 4-(methylsulfinyl)benzoate

Conditions
ConditionsYield
Stage #1: 4-(methylsulfinyl)benzoic acid; lovastatin With dicyclohexyl-carbodiimide In dichloromethane for 0.166667h; Inert atmosphere; Cooling with ice;
Stage #2: With dmap In dichloromethane at 20℃; for 16h; Inert atmosphere; Cooling with ice;		63%

Lovastatin Chemical Properties

Structure of Lovastatin (CAS NO.75330-75-5):

Empirical Formula: C24H36O5
Molecular Weight: 404.5396 
IUPAC Name: [(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate 
Index of Refraction: 1.531
Molar Refractivity: 111.71 cm3
Molar Volume: 360.6 cm3
Polarizability: 44.28×10-24cm3
Surface Tension: 43.5 dyne/cm
Density: 1.12 g/cm3
Flash Point: 185.3 °C
Enthalpy of Vaporization: 96.69 kJ/mol 
Melting Point: 175°C
Boiling Point: 559.2 °C at 760 mmHg
Vapour Pressure: 7.81E-15 mmHg at 25°C 
Water Solubility: 0.0004 mg/mL at 25 ºC 
Physical Appearance: White Solid
Product Categories: Antibiotics ; APIs ; Intermediates & Fine Chemicals ; Pharmaceuticals ; API's ; HMG-CoA reductase

Lovastatin History

    Lovastatin (CAS NO.75330-75-5) was isolated from the fungus Aspergillus terreus ,in August 1987 ,it was the first statin approved by the FDA.
    In 1998, the FDA (US Food and Drug Administration ) placed a ban on the sale of dietary supplements derived from red yeast rice, which naturally contains lovastatin, arguing that products containing prescription agents require drug approval.

Lovastatin Uses

  Lovastatin (CAS NO.75330-75-5) can be used as  hypolipidemic agent for lowering cholesterol in those with hypercholesterolemia and so preventing cardiovascular disease.In plant physiology Lovastatin (CAS NO.75330-75-5) also has occasionally been used as inhibitor of cytokinin biosynthesis.

Lovastatin Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 17mg/kg/3W-I (17mg/kg) BEHAVIORAL: WAKEFULNESS Lancet. Vol. 343, Pg. 973, 1994.
human TDLo oral 8750ug/kg/14D (8.75mg/kg) BEHAVIORAL: WAKEFULNESS

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)		 Clinical Pharmacology and Therapeutics Vol. 50, Pg. 730, 1991.
man TDLo oral 240mg/kg/60W- (240mg/kg) BEHAVIORAL: MUSCLE WEAKNESS Annals of Pharmacotherpy. Vol. 26, Pg. 190, 1992.
mouse LD50 oral > 1gm/kg (1000mg/kg)   Journal of Antibiotics. Vol. 32, Pg. 852, 1979.
women TDLo oral 285mg/kg/30W- (285mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"

LIVER: LIVER FUNCTION TESTS IMPAIRED

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"		 Israel Journal of Medical Sciences. Vol. 28, Pg. 101, 1992.

Lovastatin Safety Profile

Hazard Codes of Lovastatin (CAS NO.75330-75-5): IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-36/37/39-26 
S22:Do not breathe dust. 
S24/25:Avoid contact with skin and eyes. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: 3077
WGK Germany: 3
RTECS: EK7907000
HazardClass: 9
PackingGroup: III

Lovastatin Specification

  Lovastatin , its cas register number is 75330-75-5. It also can be called (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-3,7-dimethyl-8-(2-(2R,4R)-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl (S)-2-methyl-butyrate ; (S)-2-Methylbutyric acid, 8-ester with (4R,6R)-6-(2-((1S,2S,6R,8S,8aR)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethyl-1-naphthyl)ethyl)tetrahydro-4-hydroxy-2H-pyran-2-one ; 6-alpha-Methylcompactin ; 6alpha-Methylcompactin ; Cholestra ;
 Lipivas ; Lipofren ; Lovalip; Lovalord ; Lovasterol ; Mevinacor ; Mevinolin ; Mevlor ; Monacolin K ; Nergadan ; Paschol ; Rodatin .

Related Products

Hot Products

Post buying leads

About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia

Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog

©2008 LookChem.com,License: ICP

NO.:Zhejiang16009103

complaints:service@lookchem.com Desktop View