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

Base Information

• Chemical Name: (S)-2-Methyl-butyric acid (1S,3S,4aR,7S,8S,8aS)-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester
• CAS No.: 77517-29-4
• Molecular Formula: C₂₄H₃₈O₅
• Molecular Weight: 406.563
• Hs Code.: 2933997500
• UNII: W53N9X64FM
• ChEMBL ID: CHEMBL76114
• Mol file: 77517-29-4.mol

Synonyms:4a,5-dihydromevinolin;dihydromevinolin

Chemical Property of (S)-2-Methyl-butyric acid (1S,3S,4aR,7S,8S,8aS)-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester

Chemical Property:

• Vapor Pressure: 1.14E-13mmHg at 25°C
• Boiling Point: 534.8°C at 760 mmHg
• PKA: 13.49±0.40(Predicted)
• Flash Point: 174.5°C
• PSA: 72.83000
• Density: 1.1g/cm³
• LogP: 4.27540
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 406.27192431
• Heavy Atom Count: 29
• Complexity: 614

Purity/Quality:

98% ^*data from raw suppliers

4a,5-DihydroLovastatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(=O)OC1CC(CC2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O)C
• Isomeric SMILES: CC[C@H](C)C(=O)O[C@H]1C[C@H](C[C@H]2[C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]3C[C@H](CC(=O)O3)O)C
• Uses: 4a,5-Dihydro Lovastatin (Lovastatin EP Impurity E; Lovastatin USP Related Compound A) is an impurity in Lovastatin (L472225) bulk drug. 4a,5-Dihydro Lovastatin is an impurity in Lovastatin (L472225) bulk drug.

Technology Process of (S)-2-Methyl-butyric acid (1S,3S,4aR,7S,8S,8aS)-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester

There total 72 articles about (S)-2-Methyl-butyric acid (1S,3S,4aR,7S,8S,8aS)-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester 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: 85.0%

(1S,2S,4aR,6S,8S,8aS,3'R,5'R,2''S)-methyl-1,2,4a,5,6,7,8,8a-octahydro-3',5'-dihydroxy-2,6-dimethyl-8-<(2-methyl-1-oxobutyl)oxy>-1-naphthaleneheptanoate (101834-04-2) → (+)-Dihydromevinolin (77517-29-4)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 0.666667h; Ambient temperature;

DOI:10.1021/ja00275a053

Reference yield: 42.0%

O-benzyldihydromevinolin (129264-92-2) → (+)-Dihydromevinolin (77517-29-4)

Guidance literature:

With boron trichloride; In hexane; dichloromethane; at -78 ℃; for 4h;

DOI:10.1021/jo00309a022

Reference yield:

methyl (1S,2S,4aR,6S,8S,8aS,3'R,2''S)-3'-(tert-butyldimethylsiloxy)-7'-<1,2,4a,5,6,7,8,8a-octahydro-2,6-dimethyl-8-<(2''-methylbutyryl)oxy>-1-naphthalenyl>-5'-oxohept-6'-enoate (143633-63-0) → (+)-Dihydromevinolin (77517-29-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) triethylsilane; 2.) 48 percent aq. HF / 1.) (PPh₃)3RhCl / 1.) benzene, 70 deg C, 40 min; 2.) CH₃CN, rt. 50 min

2: 39 percent / NaBH₄ / methanol / 0.75 h / Ambient temperature

3: 85 percent / p-Ts-OH*H₂O / benzene / 0.67 h / Ambient temperature

With triethylsilane; sodium tetrahydroborate; hydrogen fluoride; toluene-4-sulfonic acid; Wilkinson's catalyst; In methanol; benzene;

DOI:10.1021/ja00275a053

upstream raw materials:

(S)-(+)-2-methylbutyric anhydride

(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

O-benzyldihydromevinolin

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

Refernces

• 1、 Hanessian,Roy,Petrini,Hodges,Di Fabio,Carganico. "Synthetic studies on the mevinic acids using the chiron approach: Total synthesis of (+)-dihydromevinolin". . p. 5766 - 5777. Retrieved 2007/10/02.
• 2、 Falck,Yang. "Total synthesis of (+)-dihydromevinolin". . p. 3563 - 3566. Retrieved 2007/10/02.