13-Methyl-8,11,13-podocarpatriene-3,12-diol

Base Information

• Chemical Name: 13-Methyl-8,11,13-podocarpatriene-3,12-diol
• CAS No.: 769140-74-1
• Molecular Formula: C18H26O2
• Molecular Weight: 274.39800
• Mol file: 769140-74-1.mol

Synonyms:

Chemical Property of 13-Methyl-8,11,13-podocarpatriene-3,12-diol

Chemical Property:

• Boiling Point: 408.7±45.0 °C(Predicted)
• PKA: 10.68±0.70(Predicted)
• PSA: 40.46000
• Density: 1.084±0.06 g/cm3(Predicted)
• LogP: 3.70160

Purity/Quality:

99% ^*data from raw suppliers

13-Methyl-8,11,13-podocarpatriene-3,12-diol ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 13-Methyl-8,11,13-podocarpatriene-3,12-diol

There total 6 articles about 13-Methyl-8,11,13-podocarpatriene-3,12-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: 74.0%

(±)-12-hydroxy-13-methylpodocarpa-8,11,13-trien-3-one → (±)-3β,12-dihydroxy-13-methylpodocarpane-8,11,13-triene (769140-74-1)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride heptahydrate; In methanol; at 0 ℃; for 0.5h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.7b00268

Reference yield:

3-ethoxy-2,6-dimethyl-2-cyclohexen-1-one (76192-88-6) → (±)-3β,12-dihydroxy-13-methylpodocarpane-8,11,13-triene (769140-74-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium dicyclohexylamide / toluene / 1.5 h / -78 °C / Inert atmosphere; Schlenk technique

1.2: 3 h / 20 °C / Inert atmosphere; Schlenk technique

2.1: cerium(III) chloride / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere; Schlenk technique

2.2: 80 °C / Inert atmosphere; Schlenk technique

3.1: boron trifluoride diethyl etherate / dichloromethane / 15 h / 50 °C / Inert atmosphere; Schlenk technique

4.1: ammonium hydroxide; lithium / tetrahydrofuran; tert-butyl alcohol / 1 h / Inert atmosphere; Schlenk technique; Cooling with acetone-dry ice

4.2: 1 h / Inert atmosphere; Schlenk technique

5.1: boron tribromide / dichloromethane / 19 h / 20 °C / Inert atmosphere; Schlenk technique; Cooling with acetone-dry ice

6.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique

With ammonium hydroxide; sodium tetrahydroborate; cerium(III) chloride; cerium(III) chloride heptahydrate; boron trifluoride diethyl etherate; boron tribromide; lithium; lithium dicyclohexylamide; In tetrahydrofuran; methanol; dichloromethane; toluene; tert-butyl alcohol;

DOI:10.1021/acs.orglett.7b00268

Reference yield:

5-bromo-2-methylphenol methyl ether (67868-73-9) → (±)-3β,12-dihydroxy-13-methylpodocarpane-8,11,13-triene (769140-74-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium dicyclohexylamide / toluene / 1.5 h / -78 °C / Inert atmosphere; Schlenk technique

1.2: 3 h / 20 °C / Inert atmosphere; Schlenk technique

2.1: cerium(III) chloride / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere; Schlenk technique

2.2: 80 °C / Inert atmosphere; Schlenk technique

3.1: boron trifluoride diethyl etherate / dichloromethane / 15 h / 50 °C / Inert atmosphere; Schlenk technique

4.1: ammonium hydroxide; lithium / tetrahydrofuran; tert-butyl alcohol / 1 h / Inert atmosphere; Schlenk technique; Cooling with acetone-dry ice

4.2: 1 h / Inert atmosphere; Schlenk technique

5.1: boron tribromide / dichloromethane / 19 h / 20 °C / Inert atmosphere; Schlenk technique; Cooling with acetone-dry ice

6.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique

With ammonium hydroxide; sodium tetrahydroborate; cerium(III) chloride; cerium(III) chloride heptahydrate; boron trifluoride diethyl etherate; boron tribromide; lithium; lithium dicyclohexylamide; In tetrahydrofuran; methanol; dichloromethane; toluene; tert-butyl alcohol;

DOI:10.1021/acs.orglett.7b00268

upstream raw materials:

3-ethoxy-2,6-dimethyl-2-cyclohexen-1-one

5-bromo-2-methylphenol methyl ether

6-Methoxy-2-oxo-1.4a.7-trimethyl-2.3.4.4a.9.10-hexahydro-phenanthren

Refernces