(-)-Phenylmenthyl (+)-O-methylpodocarpate

Base Information

• Chemical Name: (-)-Phenylmenthyl (+)-O-methylpodocarpate
• CAS No.: 154903-60-3
• Molecular Formula: C₃₄H₄₆O₃
• Molecular Weight: 502.737
• Mol file: 154903-60-3.mol

Synonyms:(-)-Phenylmenthyl (+)-O-methylpodocarpate

Chemical Property of (-)-Phenylmenthyl (+)-O-methylpodocarpate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-Phenylmenthyl (+)-O-methylpodocarpate

There total 10 articles about (-)-Phenylmenthyl (+)-O-methylpodocarpate 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: 65.0%

(1R,4aS,10aR)-6-Methoxy-1,4a-dimethyl-2-oxo-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (154903-59-0) → (-)-Phenylmenthyl (+)-O-methylpodocarpate (154903-60-3)

Guidance literature:

With hydrogenchloride; zinc; In diethyl ether; 1.) 0 deg C, 4 h, 2.) r.t., 1 h;

DOI:10.1021/jo00079a006

Reference yield:

2-acetylpropanoic acid ethyl ester (609-14-3) → (-)-Phenylmenthyl (+)-O-methylpodocarpate (154903-60-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / 4-(dimethylamino)pyridine / toluene / 120 h / Heating

2: 85 percent / LDA, DMPU / tetrahydrofuran / 1.) 0 deg C, 0.5 h, 2.) 0 deg C, 1 h

3: Mn(OAc)3*2H₂O / methanol / 8 h / 0 °C

4: 65 percent / HCl, Zn / diethyl ether / 1.) 0 deg C, 4 h, 2.) r.t., 1 h

With hydrogenchloride; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; manganese triacetate; zinc; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; toluene;

DOI:10.1021/jo00079a006

Reference yield:

3-(p-methoxyphenyl)-1-propanol (5406-18-8) → (-)-Phenylmenthyl (+)-O-methylpodocarpate (154903-60-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 82 percent / PCC / CH₂Cl₂ / 1.5 h / Ambient temperature

2: 75 percent / NaH / tetrahydrofuran / 1.) r.t., 1 h, 2.) 1 h

3: 97 percent / DIBAL / toluene; CH₂Cl₂ / Ambient temperature

4: PBr₃ / tetrahydrofuran / 0.5 h / 0 °C

5: 85 percent / LDA, DMPU / tetrahydrofuran / 1.) 0 deg C, 0.5 h, 2.) 0 deg C, 1 h

6: Mn(OAc)3*2H₂O / methanol / 8 h / 0 °C

7: 65 percent / HCl, Zn / diethyl ether / 1.) 0 deg C, 4 h, 2.) r.t., 1 h

With hydrogenchloride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; manganese triacetate; phosphorus tribromide; sodium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; zinc; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1021/jo00079a006

upstream raw materials:

(1R,4aS,10aR)-6-Methoxy-1,4a-dimethyl-2-oxo-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

2-acetylpropanoic acid ethyl ester

3-(4-methoxyphenyl)propional

3-(p-methoxyphenyl)-1-propanol

Downstream raw materials:

12-O-methylpodocarpol

12-O-methylpodocarpal

O-methylpodocarpic acid