[(1S,7S,8aR)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate

Base Information

• Chemical Name: [(1S,7S,8aR)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate
• CAS No.: 73573-88-3
• Molecular Formula: C23H34O5
• Molecular Weight: 390.52
• Hs Code.: 29322090
• NSC Number: 759322
• Mol file: 73573-88-3.mol

Synonyms:[(1S,7S,8aR)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate;Spectrum_001716;Spectrum2_001979;Spectrum3_001801;Spectrum4_001826;Spectrum5_000591;BSPBio_003381;KBioGR_002497;KBioSS_002196;DivK1c_000195;SPECTRUM1601000;SPBio_002137;HMS500J17;KBio1_000195;KBio2_002196;KBio2_004764;KBio2_007332;KBio3_002884;NINDS_000195;Pharmakon1600-01601000;CCG-39517;NSC759322;IDI1_000195;NCGC00178105-01;BRD-A83177971-001-02-4

Chemical Property of [(1S,7S,8aR)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 0Pa at 25℃
• Melting Point: 151-153 °C
• Boiling Point: 555 °C at 760 mmHg
• PKA: 13.49±0.40(Predicted)
• Flash Point: 186.5 °C
• PSA: 72.83000
• Density: 1.13 g/cm³
• LogP: 3.94950
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 20 mg/mL
• Water Solubility.: DMSO: 20 mg/mL
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 390.24062418
• Heavy Atom Count: 28
• Complexity: 637

Purity/Quality:

99% ^*data from raw suppliers

Mevastatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 22-24/25-45-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(C)C(=O)OC1CCC=C2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O
• Isomeric SMILES: CC[C@H](C)C(=O)O[C@H]1CCC=C2[C@H]1C([C@H](C=C2)C)CCC3C[C@H](CC(=O)O3)O
• Uses: A fungal metabolite which is a potent inhibitor of HMG-CoA reductase. Mevastatin (compactin) is a diterpene produced by several species of the genera Penicillium and Monascus, first reported in 1976. Mevastatin, the prtotype of the statin class, is a potent competitive inhibitor of HMG-CoA reductase, a regulatory enzyme for cholesterol biosynthesis. Mevastatin has also been shown to induce apoptosis by inhibiting post-translational prenylation of proteins such as Ras, increasing eNOS mRNA and protein levels by blocking the geranylgeranylation of Rho, and inhibiting myoblast fusion. It induces cell cycle arrest in late G1 phase and may induce bone morphogenic protein-2 (BMP-2). anti-hyperlipoproteinemic, 3-hydroxy-3-methyl glutaryl coenzyme A (HMG-CoA) reductase inhibitor

Technology Process of [(1S,7S,8aR)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate

There total 149 articles about [(1S,7S,8aR)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate 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: 70.0%

(1S,2S,8S,8aR,3'R,5'R,2''S)-methyl 1,2,6,7,8,8a-hexahydro-3',5'-dihydroxy-2-methyl-8-<(2-methyl-1-oxobutyl)oxy>-1-naphthaleneheptanoate (79814-60-1) → mevastatin (73573-88-3,58948-09-7)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 1.08333h; Ambient temperature;

DOI:10.1021/jm00393a030

Reference yield: 61.0%

(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-[2-((2R,4R)-4,6-dihydroxy-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester (116996-42-0,117065-49-3) → mevastatin (73573-88-3,58948-09-7)

Guidance literature:

With Celite; silver carbonate; In toluene; at 95 ℃; for 2h;

DOI:10.1021/ja00164a024 DOI:10.1021/ja00228a067

Reference yield: 31.0%

(1S,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-7-methyl-8-<2-((2R,4R)-tetrahydro-4-methoxy-6-oxo-2H-pyran-2-yl)-ethyl>-1-naphthyl (2S)-2-methylbutyrate (84751-53-1) → mevastatin (73573-88-3,58948-09-7)

Guidance literature:

With boron tribromide; In dichloromethane; at -23 ℃; for 5h;

DOI:10.1021/ja00279a041

upstream raw materials:

(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-[2-((2R,4R)-4,6-dihydroxy-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

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

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

(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-[2-((2R,4R,6S)-4,6-dihydroxy-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

Downstream raw materials:

acetone

tert-butyl alcohol

pravastatin sodium salt

pravastatin

Refernces

• 1、 -. "Treatment of type 1 diabetes with PDE5 inhibitors". . . Retrieved 2008/06/13.
• 2、 Hagiwara, Hisahiro,Nakano, Takashi,Kon-no, Masakazu,Uda, Hisashi. "Total synthesis of (+)-compactin by a double Michael protocol". . p. 777 - 784. Retrieved 2007/10/02.