trans-decahydro-5α-<(2,5-dimethoxyphenyl)methyl>-5β,8aβ-dimethyl-6-methylene-1-naphthalenol

Base Information

• Chemical Name: trans-decahydro-5α-<(2,5-dimethoxyphenyl)methyl>-5β,8aβ-dimethyl-6-methylene-1-naphthalenol
• CAS No.: 80765-04-4
• Molecular Formula: C₂₂H₃₂O₃
• Molecular Weight: 344.494
• Mol file: 80765-04-4.mol

Synonyms:trans-decahydro-5α-<(2,5-dimethoxyphenyl)methyl>-5β,8aβ-dimethyl-6-methylene-1-naphthalenol

Chemical Property of trans-decahydro-5α-<(2,5-dimethoxyphenyl)methyl>-5β,8aβ-dimethyl-6-methylene-1-naphthalenol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-decahydro-5α-<(2,5-dimethoxyphenyl)methyl>-5β,8aβ-dimethyl-6-methylene-1-naphthalenol

There total 3 articles about trans-decahydro-5α-<(2,5-dimethoxyphenyl)methyl>-5β,8aβ-dimethyl-6-methylene-1-naphthalenol 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: 85.0%

trans-octahydro-1α-<(2,5-dimethoxyphenyl)methyl>-1β,4aβ-dimethyl-5β-hydroxy-2(1H)-naphthalenone (80765-03-3) + Methylenetriphenylphosphorane (19493-09-5) → trans-decahydro-5α-<(2,5-dimethoxyphenyl)methyl>-5β,8aβ-dimethyl-6-methylene-1-naphthalenol (80765-04-4)

Guidance literature:

In dimethyl sulfoxide; at 75 - 80 ℃; for 40h;

DOI:10.1021/jo00348a025

Reference yield:

2,5-dimethoxybenzyl bromide (60732-17-4) → trans-decahydro-5α-<(2,5-dimethoxyphenyl)methyl>-5β,8aβ-dimethyl-6-methylene-1-naphthalenol (80765-04-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Li / 1.) NH₃ (liquid), THF, 0.5 h, 2.) 15 min

2: 85 percent / dimethylsulfoxide / 40 h / 75 - 80 °C

With lithium; In dimethyl sulfoxide;

DOI:10.1021/jo00348a025

Reference yield:

(+/-)-(4aβ,5β)-4,4a,5,6,7,8-hexahydro-5-hydroxy-1,4a-dimethylnaphthalen-2(3H)-one (24138-10-1,26742-30-3,38405-15-1,52842-07-6,102058-65-1) → trans-decahydro-5α-<(2,5-dimethoxyphenyl)methyl>-5β,8aβ-dimethyl-6-methylene-1-naphthalenol (80765-04-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Li / 1.) NH₃ (liquid), THF, 0.5 h, 2.) 15 min

2: 85 percent / dimethylsulfoxide / 40 h / 75 - 80 °C

With lithium; In dimethyl sulfoxide;

DOI:10.1021/jo00348a025

upstream raw materials:

trans-octahydro-1α-<(2,5-dimethoxyphenyl)methyl>-1β,4aβ-dimethyl-5β-hydroxy-2(1H)-naphthalenone

Methylenetriphenylphosphorane

2,5-dimethoxybenzyl bromide

(+/-)-(4aβ,5β)-4,4a,5,6,7,8-hexahydro-5-hydroxy-1,4a-dimethylnaphthalen-2(3H)-one

Downstream raw materials:

(4aS,5R,6S,8aS)-5-(2,5-Dimethoxy-benzyl)-1,5,6,8a-tetramethyl-decahydro-naphthalen-1-ol

(+/-)-avarol

trans-octahydro-5α-<(2,5-dimethoxyphenyl)methyl>-5β,6β,8aβ-trimethyl-1(2H)-naphthalenone

(+/-)-avarol dimethyl ether