5'-Chloro-6'-oxo SiMvastatin

Base Information

• Chemical Name: 5'-Chloro-6'-oxo SiMvastatin
• CAS No.: 134395-21-4
• Molecular Formula: C₂₅H₃₇ClO₆
• Molecular Weight: 469.018
• Mol file: 134395-21-4.mol

Synonyms:5'-Chloro-6'-oxo SiMvastatin

Chemical Property of 5'-Chloro-6'-oxo SiMvastatin

Chemical Property:

• Storage Temp.: Refrigerator
• Solubility.: Dichloromethane, Diethyl Ether, Ethyl Acetate

Purity/Quality:

99% ^*data from raw suppliers

5’-Chloro-6’-oxoSimvastatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Intermediate in the preparation of Simvastatin (S485000) analogs.

Technology Process of 5'-Chloro-6'-oxo SiMvastatin

There total 4 articles about 5'-Chloro-6'-oxo SiMvastatin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

6(R)-<2-<5(S)-Chloro-3-oxo-8(S)-((2,2-dimethylbutyryl)oxy)-2(S),6(R)-dimethyl-1,2,3,5,6,7,8,8a(R)-octahydronaphth-1(S)-yl>ethyl>-4(R)-((tert-butyldimethylsilyl)oxy)-3,4,5,6-tetrahydro-2H-pyran-2-one (134395-20-3) → 6(R)-<2-<5(S)-Chloro-8(S)-((2,2-dimethylbutyryl)oxy)-2(S),6(R)-dimethyl-1,2,3,5,6,7,8,8a(R)-octahydronaphth-1(S)-yl>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one (134395-21-4)

Guidance literature:

With hydrogen fluoride; In acetonitrile; at 20 ℃; for 1.5h;

DOI:10.1021/jo00099a030

Reference yield:

simvastatin (123049-81-0,79902-63-9) → 6(R)-<2-<5(S)-Chloro-8(S)-((2,2-dimethylbutyryl)oxy)-2(S),6(R)-dimethyl-1,2,3,5,6,7,8,8a(R)-octahydronaphth-1(S)-yl>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one (134395-21-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / imidazole / dimethylformamide / 1.) 0 deg C, 5 min, 2.) r.t., 5 h

2: 1.) PhSeCl, 2.) 30percent H₂O₂ / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) THF, 0 deg C, 5 min; r.t., 1 h

3: 95 percent / PCC/Al₂O₃ / toluene / 8 h / 100 °C

4: 49percent aq. HF / acetonitrile / 1.5 h / 20 °C

With 1H-imidazole; aluminum oxide; Phenylselenyl chloride; hydrogen fluoride; dihydrogen peroxide; pyridinium chlorochromate; In N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo00099a030

Reference yield:

6(R)-<2-<8(S)-((2,2-Dimethylbutyryl)oxy)-2(S),6(R)-dimethyl-1,2,6,7,8,8a(R)-hexahydronaphth-1(S)-yl>ethyl>-4(R)-((tert-butyldimethylsilyl)oxy)-3,4,5,6-tetrahydro-2H-pyran-2-one (79902-59-3) → 6(R)-<2-<5(S)-Chloro-8(S)-((2,2-dimethylbutyryl)oxy)-2(S),6(R)-dimethyl-1,2,3,5,6,7,8,8a(R)-octahydronaphth-1(S)-yl>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one (134395-21-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) PhSeCl, 2.) 30percent H₂O₂ / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) THF, 0 deg C, 5 min; r.t., 1 h

2: 95 percent / PCC/Al₂O₃ / toluene / 8 h / 100 °C

3: 49percent aq. HF / acetonitrile / 1.5 h / 20 °C

With aluminum oxide; Phenylselenyl chloride; hydrogen fluoride; dihydrogen peroxide; pyridinium chlorochromate; In toluene; acetonitrile;

DOI:10.1021/jo00099a030

upstream raw materials:

6(R)-<2-<5(S)-Chloro-3-oxo-8(S)-((2,2-dimethylbutyryl)oxy)-2(S),6(R)-dimethyl-1,2,3,5,6,7,8,8a(R)-octahydronaphth-1(S)-yl>ethyl>-4(R)-((tert-butyldimethylsilyl)oxy)-3,4,5,6-tetrahydro-2H-pyran-2-one

simvastatin

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