3,5-Dihydroxy-7-[(1S,2S,4aR,8S,8aS)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-heptanoic acid methyl ester

Base Information

• Chemical Name: 3,5-Dihydroxy-7-[(1S,2S,4aR,8S,8aS)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-heptanoic acid methyl ester
• CAS No.: 143168-96-1
• Molecular Formula: C₂₄H₄₀O₆
• Molecular Weight: 424.578
• Mol file: 143168-96-1.mol

Synonyms:

Chemical Property of 3,5-Dihydroxy-7-[(1S,2S,4aR,8S,8aS)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-heptanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5-Dihydroxy-7-[(1S,2S,4aR,8S,8aS)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-heptanoic acid methyl ester

There total 1 articles about 3,5-Dihydroxy-7-[(1S,2S,4aR,8S,8aS)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-heptanoic acid methyl 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:

5-Hydroxy-7-[(1S,2S,4aR,8S,8aS)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-3-oxo-heptanoic acid methyl ester (143112-44-1,143112-45-2) → 3,5-Dihydroxy-7-[(1S,2S,4aR,8S,8aS)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-heptanoic acid methyl ester (143112-46-3,143168-96-1) + (S)-2-Methyl-butyric acid (1S,4aR,7S,8S,8aS)-8-[2-(2-ethyl-6-methoxycarbonylmethyl-[1,3,2]dioxaborinan-4-yl)-ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester

Guidance literature:

With sodium tetrahydroborate; diethyl methoxy borane; Yield given. Multistep reaction. Yields of byproduct given; 1) THF, methanol, room temperature, 15 min; 2) THF, methanol, -78 --> room temperature;

DOI:10.1039/P19940002417

Reference yield: 26.0%

3,5-Dihydroxy-7-[(1S,2S,4aR,8S,8aS)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-heptanoic acid methyl ester (143112-46-3,143168-96-1) → (+)-dihydrocompactin (78366-44-6) + 3,5-epidihydrocompactin (143168-97-2)

Guidance literature:

With pyridine; hydrogen fluoride; In acetonitrile; for 1h; Ambient temperature;

DOI:10.1039/P19940002417

Reference yield:

3,5-Dihydroxy-7-[(1S,2S,4aR,8S,8aS)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-heptanoic acid methyl ester (143112-46-3,143168-96-1) → (1S,2S,4aR,8S,8aS)-8-acetoxy-1-<(3'S,5'R)-3'-acetoxy-5',7'-bis(p-bromobenzoyloxy)heptyl>-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene

Guidance literature:

Multi-step reaction with 8 steps

1: 26 percent / HF, pyridine / acetonitrile / 1 h / Ambient temperature

2: 79 percent / pyridinium toluene-p-sulfonate / CH₂Cl₂ / Ambient temperature

3: 21.1 mg / LiAlH₄ / diethyl ether / 6.5 h / Ambient temperature

4: Et₃N, 4-dimethylaminopyridine / dimethylformamide / Ambient temperature

5: 100 percent / pyridine, 4-dimethylaminopyridine / Ambient temperature

6: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

7: 5.8 mg / pyridinium toluene-p-sulfonate / aq. ethanol / 5 h / Heating

8: 4-dimethylaminopyridine / pyridine / Ambient temperature

With pyridine; dmap; lithium aluminium tetrahydride; hydrogen fluoride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; pyridine; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/P19940002417

upstream raw materials:

5-Hydroxy-7-[(1S,2S,4aR,8S,8aS)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-3-oxo-heptanoic acid methyl ester

Downstream raw materials:

(+)-dihydrocompactin

3,5-epidihydrocompactin

(1S,4aR,7S,8S,8aS)-8-[(3S,5R)-7-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-5-(tetrahydro-pyran-2-yloxy)-heptyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol

(1S,2S,4aR,8S,8aS)-8-acetoxy-1-<(3'S,5'R)-3'-acetoxy-7'-(tert-butyldiphenylsiloxy)-5'-(tetrahydropyran-2-yloxy)heptyl>-2-methyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene