4-tert-Butyldimethylsilyl-4a'-hydroxy Simvastatin

Base Information

• Chemical Name: 4-tert-Butyldimethylsilyl-4a'-hydroxy Simvastatin
• CAS No.: 125142-16-7
• Molecular Formula: C₃₁H₅₄O₆Si
• Molecular Weight: 550.852
• DSSTox Substance ID: DTXSID50434013
• Wikidata: Q82248305
• Mol file: 125142-16-7.mol

Synonyms:4-tert-Butyldimethylsilyl-4a'-hydroxy Simvastatin;125142-16-7;[(1S,3R,4aS,7S,8S,8aS)-8-[2-[(2R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-6-oxooxan-2-yl]ethyl]-4a-hydroxy-3,7-dimethyl-2,3,4,7,8,8a-hexahydro-1H-naphthalen-1-yl] 2,2-dimethylbutanoate;SCHEMBL8973489;DTXSID50434013;AKOS030254492;4-Tert-Butyldimethylsilyl-4a/'-hydroxy Simvastatin;J-005204

Chemical Property of 4-tert-Butyldimethylsilyl-4a'-hydroxy Simvastatin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 88-92°C
• Refractive Index: 1.506
• Boiling Point: 592.305°C at 760 mmHg
• PKA: 13.95±0.70(Predicted)
• Flash Point: 312.015°C
• PSA: 82.06000
• Density: 1.055g/cm³
• LogP: 6.80990
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 550.36896597
• Heavy Atom Count: 38
• Complexity: 889

Purity/Quality:

98%Min ^*data from raw suppliers

4-tert-Butyldimethylsilyl-4a’-hydroxySimvastatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)(C)C(=O)OC1CC(CC2(C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O[Si](C)(C)C(C)(C)C)O)C
• Isomeric SMILES: CCC(C)(C)C(=O)O[C@H]1C[C@H](C[C@]2([C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]3C[C@H](CC(=O)O3)O[Si](C)(C)C(C)(C)C)O)C
• Uses: Intermediate for the Simvastatin hydroxymethyl metabolite preparation

Technology Process of 4-tert-Butyldimethylsilyl-4a'-hydroxy Simvastatin

There total 7 articles about 4-tert-Butyldimethylsilyl-4a'-hydroxy 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: 92.0%

2,2-Dimethyl-butyric acid (1S,3R,4aS,7S,8S,8aS)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-4-chloro-4a-hydroxy-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester (123852-10-8) → 6(R)-<2-<4a(S)-Hydroxy-8(S)-((2,2-dimethylbutyryl)oxy)-2(S),6(R)-dimethyl-1,2,4a,5,6,7,8,8a(S)-octahydronaphth-1(S)-yl>ethyl>-4(R)-((tert-butyldimethylsilyl)oxy)-3,4,5,6-tetrahydro-2H-pyran-2-one (125142-16-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; Heating;

DOI:10.1021/jo00033a012

Reference yield: 92.0%

6(R)-<2-<5(S)-Chloro-4a(S)-hydroxy-8(S)-((2,2-dimethylbutyryl)oxy)-2(S),6(R)-dimethyl-1,2,4a,5,6,7,8,8a(S)-octahydronaphth-1(S)-yl>ethyl>-4(R)-((tert-butyldimethylsilyl)oxy)-3,4,5,6-tetrahydro-2H-pyran-2-one → 6(R)-<2-<4a(S)-Hydroxy-8(S)-((2,2-dimethylbutyryl)oxy)-2(S),6(R)-dimethyl-1,2,4a,5,6,7,8,8a(S)-octahydronaphth-1(S)-yl>ethyl>-4(R)-((tert-butyldimethylsilyl)oxy)-3,4,5,6-tetrahydro-2H-pyran-2-one (125142-16-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); n-Bu₄SnH; In benzene; for 2h; Heating;

DOI:10.1021/jo00099a030

Reference yield:

simvastatin (123049-81-0,79902-63-9) → 6(R)-<2-<4a(S)-Hydroxy-8(S)-((2,2-dimethylbutyryl)oxy)-2(S),6(R)-dimethyl-1,2,4a,5,6,7,8,8a(S)-octahydronaphth-1(S)-yl>ethyl>-4(R)-((tert-butyldimethylsilyl)oxy)-3,4,5,6-tetrahydro-2H-pyran-2-one (125142-16-7)

Guidance literature:

Multi-step reaction with 3 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: 92 percent / n-Bu₄SnH, AIBN / benzene / 2 h / Heating

With 1H-imidazole; Phenylselenyl chloride; 2,2'-azobis(isobutyronitrile); n-Bu₄SnH; dihydrogen peroxide; In N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00099a030

upstream raw materials:

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

simvastatin

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

2,2-Dimethyl-butyric acid (1S,4S,5S,6S,7S,9R)-5-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-4-methyl-11-oxa-tricyclo[7.2.1.0^1,6]dodec-2-en-7-yl ester

6’-hydroxymethyl simvistatin

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