(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
• General Description: Dihydromevinolin, also known as dihydrolovastatin or L 154883, is a biologically active compound that functions as an HMG-CoA reductase inhibitor, effectively blocking the rate-limiting step in cholesterol biosynthesis. Its structure includes a decalin system, which is a critical feature shared among mevinic acids, contributing to its pharmacological activity. The synthesis of its optically pure intermediates, such as through intramolecular Diels-Alder reactions, highlights its complex stereochemistry and importance in medicinal chemistry for cholesterol management.

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

Access to an optically pure key intermediate of dihydromevinolin

10.1016/S0040-4039(00)73243-6

The research aimed to develop an efficient route to optically pure key intermediates of dihydromevinolin, which are biologically active compounds known for their ability to inhibit HMG CoA reductase, a rate-limiting enzyme in cholesterol synthesis in humans. The researchers focused on the intramolecular Diels-Alder (MDA) reaction as the most promising approach for constructing the decalin system present in mevinic acids. They successfully synthesized the key intermediate through a series of chemical reactions starting from (R)-5-methyl-2-cyclohexanone, involving vinylmagnesium bromide, MnO2, LiAlH4, propargyl bromide, t-BuOK, 10-camphorsulphonic acid (CSA), BH3*THF, NaOH, H2O2, Jones reagent, and other reagents.