2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-prop-2-en-1-ol

Base Information

• Chemical Name: 2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-prop-2-en-1-ol
• CAS No.: 132101-61-2
• Molecular Formula: C₂₃H₃₂O₃
• Molecular Weight: 356.505
• Mol file: 132101-61-2.mol

Synonyms:2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-prop-2-en-1-ol

Chemical Property of 2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-prop-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-prop-2-en-1-ol

There total 4 articles about 2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-prop-2-en-1-ol 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: 93.0%

tert-Butyl-{2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-allyloxy}-dimethyl-silane (132101-60-1) → 2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-prop-2-en-1-ol (132101-61-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 16h; Ambient temperature;

DOI:10.1021/ja00008a044

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → 2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-prop-2-en-1-ol (132101-61-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DME, RT, 30 min, 2.) reflux, 18 h

2: 93 percent / n-Bu₄NF / tetrahydrofuran / 16 h / Ambient temperature

With tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran;

DOI:10.1021/ja00008a044

Reference yield:

(1R,3R,3aR,3bR,4R,6aS,6bR)-3-[1-(tert-Butyl-dimethyl-silanyloxymethyl)-vinyl]-4,6b-dimethyl-decahydro-cyclobutadicyclopenten-1-ol (132101-59-8) → 2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-prop-2-en-1-ol (132101-61-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DME, RT, 30 min, 2.) reflux, 18 h

2: 93 percent / n-Bu₄NF / tetrahydrofuran / 16 h / Ambient temperature

With tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran;

DOI:10.1021/ja00008a044

upstream raw materials:

tert-Butyl-{2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-allyloxy}-dimethyl-silane

p-Methoxybenzyl bromide

(1R,3R,3aR,3bR,4R,6aS,6bR)-3-[1-(tert-Butyl-dimethyl-silanyloxymethyl)-vinyl]-4,6b-dimethyl-decahydro-cyclobutadicyclopenten-1-ol

(1R,3R,3aR,3bR,4R,6aS,6bR)-3-(1-Hydroxymethyl-vinyl)-4,6b-dimethyl-decahydro-cyclobutadicyclopenten-1-ol

Downstream raw materials:

2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-propenal

(E)-(S)-6-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-2-methyl-hepta-3,6-diene-2,5-diol

(E)-(S)-6-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-2-methyl-5-triethylsilanyloxy-hepta-3,6-dien-2-ol

Methanesulfonic acid (R)-1-[(2R,3R)-3-(1-hydroxy-1-methyl-ethyl)-oxiranyl]-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-allyl ester