7-[2,6-Dimethyl-8-(2-methyl-1-oxobutoxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid

Base Information

• Chemical Name: 7-[2,6-Dimethyl-8-(2-methyl-1-oxobutoxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid
• CAS No.: 137767-34-1
• Molecular Formula: C₂₄H₃₈O₆
• Molecular Weight: 422.562
• DSSTox Substance ID: DTXSID40868444
• Nikkaji Number: J460.716C
• Wikidata: Q27166734
• ChEMBL ID: CHEMBL3187243
• Mol file: 137767-34-1.mol

Synonyms:1-Naphthaleneheptanoic acid,1,2,6,7,8,8a-hexahydro-b,d-dihydroxy-2,6-dimethyl-8-[(2S)-2-methyl-1-oxobutoxy]-, (bR,dR,1S,2S,6R,8S,8aR)-;SCHEMBL4320913;CHEMBL3187243;ACon1_000849;CHEBI:94971;DTXSID40868444;NCGC00169298-01;NCGC00169298-03;L-665465;BRD-A70155556-001-01-0;BRD-A70155556-001-03-6;BRD-A70155556-001-04-4;Q27166734;137767-34-1;7-[2,6-dimethyl-8-(2-methyl-1-oxobutoxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid;7-{2,6-Dimethyl-8-[(2-methylbutanoyl)oxy]-1,2,6,7,8,8a-hexahydronaphthalen-1-yl}-3,5-dihydroxyheptanoic acid

Chemical Property of 7-[2,6-Dimethyl-8-(2-methyl-1-oxobutoxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid

Chemical Property:

• XLogP3: 3.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 422.26683893
• Heavy Atom Count: 30
• Complexity: 654

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC(CC(CC(=O)O)O)O)C

Technology Process of 7-[2,6-Dimethyl-8-(2-methyl-1-oxobutoxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid

There total 6 articles about 7-[2,6-Dimethyl-8-(2-methyl-1-oxobutoxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid 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:

lovastatin (75330-75-5,79952-44-6) → lovastatin acid (75225-51-3,137767-34-1,76556-02-0,77285-87-1) + (4R,6R)-4-hydroxy-6-(2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl)tetrahydro-2H-pyran-2-one (151006-15-4,79952-42-4,76343-78-7,81739-25-5) + (3R,5R)-3,5-dihydroxy-7-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)heptanoic acid (132748-10-8)

Guidance literature:

lovastatin; With methanol; sodium hydroxide; 2,6-di-tert-butyl-4-methyl-phenol; at 50 ℃; for 1h;

With methanol; ammonia; water; lovastatin esterase; at 40 ℃; for 43h; pH=9.5;

With hydrogenchloride; In methanol; water; at 12 ℃; pH=2.5;

Reference yield:

lovastatin (75330-75-5,79952-44-6) → lovastatin acid (75225-51-3,137767-34-1,76556-02-0,77285-87-1)

Guidance literature:

With sodium hydroxide; at 20 ℃; for 0.5h;

DOI:10.1002/1520-6017(200012)89:12<1594::AID-JPS11>3.0.CO;2-5

Reference yield:

(3R,5R)-3,5-dihydroxy-7-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)heptanoic acid (132748-10-8) → lovastatin acid (75225-51-3,137767-34-1,76556-02-0,77285-87-1)

Guidance literature:

With LovD; pH=7.9; Kinetics; aq. buffer;

upstream raw materials:

lovastatin

α-S-methylbutyryl-CoA

(3R,5R)-3,5-dihydroxy-7-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)heptanoic acid

α-S-methylbutyryl-S-N-acetylcysteamine

Downstream raw materials:

(1S,3R,7S,8S,8αR)-8-(2-((2R,4R)-4-((tert-butyldimethylchlorosilane)oxy)-6-oxohexahydro-2H-pyran-2-yl)ethyl)-3,7-dimethyl-1,2,3,7,8,8α-hexahydronaphthalene-1-yl(4-nitrophenyl)carbonate

(4R,6R)-6-[2-((1S,2S,6R,8S,8aR)-8-[((4-ethynylphenyl)carbamoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthyl)ethyl]-4-[(tert-butyldimethylsilyl)oxy]-3,4,5,6-tetrahydro-2H-pyran-2-one

(4R,6R)-6-[2-((1S,2S,6R,8S,8aR)-8-[((4-ethynylbenzyl)carbamoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthyl)ethyl]-4-[(tert-butyldimethylsilyl)oxy]-3,4,5,6-tetrahydro-2H-pyran-2-one

(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

Refernces

• 1、 Harrison, Angela T.,Kriel, Frederik H.,Papathanasopoulos, Maria A.,Mosebi, Salerwe,Abrahams, Shaakira,Hewer, Raymond. "The evaluation of statins as potential inhibitors of the LEDGF/p75-HIV-1 integrase interaction". . p. 290 - 295. Retrieved 2015.
• 2、 Kobayashi, Masaki,Chisaki, Ikumi,Narumi, Katsuya,Hidaka, Kazuhiro,Kagawa, Toshiki,Itagaki, Shirou,Hirano, Takeshi,Iseki, Ken. "Association between risk of myopathy and cholesterol-lowering effect: A comparison of all statins". . p. 969 - 975. Retrieved 2008.
• 3、 Xie, Xinkai,Meehan, Michael J.,Xu, Wei,Dorrestein, Pieter C.,Tang, Yi. "Acyltransferase mediated polyketide release from a fungal megasynthase". supporting information; experimental part. p. 8388 - 8389. Retrieved 2009/10/24.