3,5-Dihydroxy-7-[2-methyl-8-(2-methylbutanoyloxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]heptanoic acid

Base Information

• Chemical Name: 3,5-Dihydroxy-7-[2-methyl-8-(2-methylbutanoyloxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]heptanoic acid
• CAS No.: 84064-38-0
• Molecular Formula: C₂₃H₃₆O₆
• Molecular Weight: 408.535
• DSSTox Substance ID: DTXSID40875476
• Nikkaji Number: J20.886H
• Wikidata: Q103816905
• Mol file: 84064-38-0.mol

Synonyms:SCHEMBL10685062;DTXSID40875476;CHEBI:182376;3,5-dihydroxy-7-[2-methyl-8-(2-methylbutanoyloxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]heptanoic acid;InChI=1/C23H36O6/c1-4-14(2)23(28)29-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-17(24)12-18(25)13-21(26)27/h6,8-9,14-15,17-20,22,24-25H,4-5,7,10-13H2,1-3H3,(H,26,27

Chemical Property of 3,5-Dihydroxy-7-[2-methyl-8-(2-methylbutanoyloxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]heptanoic acid

Chemical Property:

• PSA: 104.06000
• LogP: 3.46960
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 408.25118886
• Heavy Atom Count: 29
• Complexity: 625

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(=O)OC1CCC=C2C1C(C(C=C2)C)CCC(CC(CC(=O)O)O)O
• General Description: (3R,5R)-7-[1,2,6,7,8,8aβ-Hexahydro-8α-[[(2S)-2-methylbutyryl]oxy]-2β-methylnaphthalene-1β-yl]-3,5-dihydroxyheptanoic acid is a key intermediate in the synthesis of dihydromevinolin, a biologically active compound that inhibits HMG-CoA reductase, an enzyme critical for cholesterol biosynthesis. This intermediate features a decalin core with stereospecific substitutions, including a (2S)-2-methylbutyryloxy group at the 8α-position and a 2β-methyl group, along with a 3,5-dihydroxyheptanoic acid side chain. Its synthesis involves an intramolecular Diels-Alder reaction and multiple stereoselective transformations to achieve the desired optically pure configuration. (3R,5R)-7-[1,2,6,7,8,8aβ-Hexahydro-8α-[[(2S)-2-methylbutyryl]oxy]-2β-methylnaphthalene-1β-yl]-3,5-dihydroxyheptanoic acid serves as a precursor for mevinic acids, highlighting its importance in cholesterol-lowering drug development.

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.

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