pimara-8(14),15-diene-3,7-diol

Base Information

• Chemical Name: pimara-8(14),15-diene-3,7-diol
• CAS No.: 110268-98-9
• Molecular Formula: C₂₀H₃₂O₂
• Molecular Weight: 304.473
• Mol file: 110268-98-9.mol

Synonyms:2,9-Phenanthrenediol,7-ethenyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-1,1,4a,7-tetramethyl-,[2R-(2a,4aa,4bb,7b,9b,10ab)]-; (+)-Oryzalexin D; 3,7-Dihydroxy-(+)-sandaracopimaradiene; OryzalexinD

Chemical Property of pimara-8(14),15-diene-3,7-diol

Chemical Property:

• Vapor Pressure: 1.36E-08mmHg at 25°C
• Boiling Point: 414.3°Cat760mmHg
• Flash Point: 181.8°C
• PSA: 63.63000
• Density: 1.05g/cm³
• LogP: 6.70700

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of pimara-8(14),15-diene-3,7-diol

There total 7 articles about pimara-8(14),15-diene-3,7-diol 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:

(+/-) - 3β-hydroxyisopimara-8(14),15-diene (4728-30-7,30294-96-3,57651-53-3,84108-06-5,106036-76-4,112065-73-3,112065-74-4) → (+/-)-3β,7α-dihydroxyisopimara-8(14),15-diene (98063-15-1,106036-79-7,110268-98-9,110658-39-4,110900-74-8,112420-53-8,112709-67-8)

Guidance literature:

With potassium hydroxide; In methanol;

DOI:10.1016/S0040-4020(01)91369-9

Reference yield:

(+/-) - 13-butylthiomethylene-3α-hydroxy-4α,4β,10α-trimethyl-14-oxo-5β,8α,9β-perhydrophenanthrene (105996-89-2) → (+/-)-3β,7α-dihydroxyisopimara-8(14),15-diene (98063-15-1,106036-79-7,110268-98-9,110658-39-4,110900-74-8,112420-53-8,112709-67-8)

Guidance literature:

Multi-step reaction with 6 steps

1: imidazole / dimethylformamide / 20 h / 25 - 30 °C

2: 1.)NaBH₄ 2.)CdCO₃, HgCl₂ / 1.)EtOH, THF, 2 h, 10 deg C_. 2.)EtOH, reflux, 5 min

3: t-BuOK / benzene; 2-methyl-propan-2-ol / 1 h

4: 1.)n-BuLi / 1.)Hexane, THF, 10 min, 0-5 deg C_. 2.)THF, overnight room temp.

5: aq HF / acetonitrile / 1.5 h / Ambient temperature

6: KOH / methanol

With 1H-imidazole; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; cadmium(II) carbonate; hydrogen fluoride; potassium tert-butylate; mercury dichloride; In methanol; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4020(01)91369-9

Reference yield:

Formic acid (4aR,4bS,8aR,10aR)-7-[1-butylsulfanyl-meth-(Z)-ylidene]-1,1,4a-trimethyl-8-oxo-tetradecahydro-phenanthren-2-yl ester (105996-90-5) → (+/-)-3β,7α-dihydroxyisopimara-8(14),15-diene (98063-15-1,106036-79-7,110268-98-9,110658-39-4,110900-74-8,112420-53-8,112709-67-8)

Guidance literature:

Multi-step reaction with 7 steps

1: KOH / methanol; H₂O

2: imidazole / dimethylformamide / 20 h / 25 - 30 °C

3: 1.)NaBH₄ 2.)CdCO₃, HgCl₂ / 1.)EtOH, THF, 2 h, 10 deg C_. 2.)EtOH, reflux, 5 min

4: t-BuOK / benzene; 2-methyl-propan-2-ol / 1 h

5: 1.)n-BuLi / 1.)Hexane, THF, 10 min, 0-5 deg C_. 2.)THF, overnight room temp.

6: aq HF / acetonitrile / 1.5 h / Ambient temperature

7: KOH / methanol

With 1H-imidazole; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; cadmium(II) carbonate; hydrogen fluoride; potassium tert-butylate; mercury dichloride; In methanol; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4020(01)91369-9

upstream raw materials:

(+/-) - 3β-hydroxyisopimara-8(14),15-diene

(+/-) - 13-butylthiomethylene-3α-hydroxy-4α,4β,10α-trimethyl-14-oxo-5β,8α,9β-perhydrophenanthrene

Formic acid (4aR,4bS,8aR,10aR)-7-[1-butylsulfanyl-meth-(Z)-ylidene]-1,1,4a-trimethyl-8-oxo-tetradecahydro-phenanthren-2-yl ester

tert-Butyl-dimethyl-((2S,4aR,4bS,10aR)-1,1,4a,7-tetramethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-phenanthren-2-yloxy)-silane

Refernces