1-Naphthaleneheptanoic acid, 1,2,6,7,8,8a-hexahydro-beta,delta-dihydroxy-2-methyl-8-(2-methyl-1-oxobutoxy)-, methyl ester

Base Information

• Chemical Name: 1-Naphthaleneheptanoic acid, 1,2,6,7,8,8a-hexahydro-beta,delta-dihydroxy-2-methyl-8-(2-methyl-1-oxobutoxy)-, methyl ester
• CAS No.: 67383-81-7
• Molecular Formula: C₂₄H₃₈O₆
• Molecular Weight: 422.562
• DSSTox Substance ID: DTXSID30986666
• Mol file: 67383-81-7.mol

Synonyms:Methyl compactin;67383-81-7;1-Naphthaleneheptanoic acid, 1,2,6,7,8,8a-hexahydro-beta,delta-dihydroxy-2-methyl-8-(2-methyl-1-oxobutoxy)-, methyl ester;DTXSID30986666;METHYL 3,5-DIHYDROXY-7-{2-METHYL-8-[(2-METHYLBUTANOYL)OXY]-1,2,6,7,8,8A-HEXAHYDRONAPHTHALEN-1-YL}HEPTANOATE

Chemical Property of 1-Naphthaleneheptanoic acid, 1,2,6,7,8,8a-hexahydro-beta,delta-dihydroxy-2-methyl-8-(2-methyl-1-oxobutoxy)-, methyl ester

Chemical Property:

• Vapor Pressure: 4.51E-15mmHg at 25°C
• Boiling Point: 564.1°Cat760mmHg
• Flash Point: 183.9°C
• Density: 1.12g/cm³
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 422.26683893
• Heavy Atom Count: 30
• Complexity: 640

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)OC)O)O

Technology Process of 1-Naphthaleneheptanoic acid, 1,2,6,7,8,8a-hexahydro-beta,delta-dihydroxy-2-methyl-8-(2-methyl-1-oxobutoxy)-, methyl ester

There total 90 articles about 1-Naphthaleneheptanoic acid, 1,2,6,7,8,8a-hexahydro-beta,delta-dihydroxy-2-methyl-8-(2-methyl-1-oxobutoxy)-, 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: 63.0%

5-Hydroxy-7-[(1S,2S,8S,8aR)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-3-oxo-heptanoic acid methyl ester (79782-56-2,79782-57-3,85738-03-0) → 3,5-Dihydroxy-7-[(1S,2S,8S,8aR)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-heptanoic acid methyl ester (67383-81-7,79814-60-1,79896-19-8,79896-20-1,79896-21-2,109785-25-3,109785-26-4)

Guidance literature:

With zinc(II) tetrahydroborate; In hexane; at 0 ℃; for 1h;

DOI:10.1021/ja00411a063

Reference yield:

1β,4α-bis(benzyloxy)-1,2,3,4,4aβ,5,8,8aα-octahydronaphthalene (84131-75-9) → (S)-3,5-Dihydroxy-7-[(1S,2S,8S,8aR)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-heptanoic acid methyl ester (67383-81-7,79814-60-1,79896-19-8,79896-20-1,79896-21-2,109785-25-3,109785-26-4)

Guidance literature:

Multi-step reaction with 19 steps

1: 32 g / acetic acid / 1 h / 25 °C

2: 88 percent / 4percent KOH / methanol; diethyl ether / 2 h / 25 °C

3: 30percent H₂O₂ / tetrahydrofuran; H₂O / 2.5 h / 25 °C

4: tetrahydrofuran; H₂O / 2 h / 55 °C

5: 20.6 g / Jones reagent / tetrahydrofuran; H₂O; acetone / 0.25 h

6: 1.) THF, -20 deg C, 30 min, 2.) -78 deg C

7: 38 g / Et₃N / CH₂Cl₂ / 0.5 h / -5 °C

8: 28.09 g / DBU / benzene / 1 h / 25 °C

9: 78 percent / H₂ / 10percent Pd/C / benzene; pyridine / 0.67 h / 25 °C

10: Et₃N, Na₂SO₄ / ethanol / 7 h / 25 °C

11: 5.3 g / LDA / tetrahydrofuran; hexane / -78 deg C -> 0 deg C, 1 h; 0 deg C, 4 h

12: 100 percent / Li, NH₃ liq. / tetrahydrofuran / 0.5 h

13: 1 mg / 4-(dimethylamino)pyridine / pyridine / 16 h / 25 °C

14: 2.8 g / pyridine / 8 h / 0 °C

15: 1.8 g / DBU / pyridine / 3 h / Heating

16: 1.44 g / acetic acid; tetrahydrofuran; H₂O / 8 h / 25 °C

17: 65 percent / pyridinium chlorochromate / CH₂Cl₂ / 4 h / 25 °C

18: 1.) NaH, 2.) n-BuLi / 1.) THF, 0 deg C, 10 min, 2.) THF-hexane, 0 deg C, 10 min, 3.) 0 deg C, 15 min

19: 16 mg / Zn(BH₄)2 / diethyl ether / 1 h / 25 °C

With dmap; potassium hydroxide; n-butyllithium; jones reagent; zinc(II) tetrahydroborate; ammonia; hydrogen; dihydrogen peroxide; lithium; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium sulfate; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; acetic acid; acetone; benzene;

DOI:10.1021/ja00341a046

Reference yield:

1β,4α-bis(benzyloxy)-1,2,3,4,4aβ,5,8,8aα-octahydronaphthalene (84131-75-9) → (R)-3,5-Dihydroxy-7-[(1S,2S,8S,8aR)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-heptanoic acid methyl ester (67383-81-7,79814-60-1,79896-19-8,79896-20-1,79896-21-2,109785-25-3,109785-26-4)

Guidance literature:

Multi-step reaction with 19 steps

1: 32 g / acetic acid / 1 h / 25 °C

2: 88 percent / 4percent KOH / methanol; diethyl ether / 2 h / 25 °C

3: 30percent H₂O₂ / tetrahydrofuran; H₂O / 2.5 h / 25 °C

4: tetrahydrofuran; H₂O / 2 h / 55 °C

5: 20.6 g / Jones reagent / tetrahydrofuran; H₂O; acetone / 0.25 h

6: 1.) THF, -20 deg C, 30 min, 2.) -78 deg C

7: 38 g / Et₃N / CH₂Cl₂ / 0.5 h / -5 °C

8: 28.09 g / DBU / benzene / 1 h / 25 °C

9: 78 percent / H₂ / 10percent Pd/C / benzene; pyridine / 0.67 h / 25 °C

10: Et₃N, Na₂SO₄ / ethanol / 7 h / 25 °C

11: 5.3 g / LDA / tetrahydrofuran; hexane / -78 deg C -> 0 deg C, 1 h; 0 deg C, 4 h

12: 100 percent / Li, NH₃ liq. / tetrahydrofuran / 0.5 h

13: 1 mg / 4-(dimethylamino)pyridine / pyridine / 16 h / 25 °C

14: 2.8 g / pyridine / 8 h / 0 °C

15: 1.8 g / DBU / pyridine / 3 h / Heating

16: 1.44 g / acetic acid; tetrahydrofuran; H₂O / 8 h / 25 °C

17: 65 percent / pyridinium chlorochromate / CH₂Cl₂ / 4 h / 25 °C

18: 1.) NaH, 2.) n-BuLi / 1.) THF, 0 deg C, 10 min, 2.) THF-hexane, 0 deg C, 10 min, 3.) 0 deg C, 15 min

19: 34 mg / Zn(BH₄)2 / diethyl ether / 1 h / 25 °C

With dmap; potassium hydroxide; n-butyllithium; jones reagent; zinc(II) tetrahydroborate; ammonia; hydrogen; dihydrogen peroxide; lithium; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium sulfate; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; acetic acid; acetone; benzene;

DOI:10.1021/ja00341a046

upstream raw materials:

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

(4aR,5S,8R,8aS)-5-Hydroxy-8-methoxy-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one

Acetic acid (1R,4S,4aR,5S,6S,8aS)-5-allyl-4-hydroxy-6-methyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl ester

(4aR,5S,8R,8aS)-8-Methoxy-5-trimethylsilanyloxy-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one

Downstream raw materials:

mevastatin

3,5-bis-epi-compactin

3-epi-compactin

5-epi-compactin

Refernces

• 1、 Haruyama,Kuwano,Kinoshita,Terahara,Nishigaki,Tamura. "Structure elucidation of the bioactive metabolites of ML-236B (mevastatin) isolated from dog urine". . p. 1459 - 1467. Retrieved 2007/10/02.
• 2、 Wang,Hsu,Sih. "Total synthesis of (+)-compactin (ML-236B)". . p. 6538 - 6539. Retrieved 2007/12/18.