(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

Base Information

Chemical Name:(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
CAS No.:127135-76-6
Molecular Formula:C₂₈H₄₀O₄
Molecular Weight:440.623
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 8 articles about (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 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: 100.0%

: 127135-70-0
(E)-(S)-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-6-methyl-6-triethylsilanyloxy-hepta-1,4-dien-3-ol

: 127135-76-6
(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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 20h; Ambient temperature;
DOI:10.1021/ja00008a044

Reference yield:

: 127156-24-5
2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-propenal

: 127135-76-6
(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

Guidance literature:: Multi-step reaction with 2 steps

1: 78 percent

2: Bu₄NF

With tetrabutyl ammonium fluoride;
DOI:10.1016/S0040-4039(01)80758-9

Reference yield:

: 2746-25-0
p-Methoxybenzyl bromide

: 127135-76-6
(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

Guidance literature:: Multi-step reaction with 5 steps

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

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

3: 94 percent / MnO₂ / CH₂Cl₂ / 24 h / Ambient temperature

4: 1.) n-BuLi / 1.) THF, hexane, a) -78 deg C, 2 h, b) -10 deg C, 1 h, 2.) -78 deg C to RT, 4 h

5: 100 percent / n-Bu₄NF / tetrahydrofuran / 20 h / Ambient temperature

With manganese(IV) oxide; n-butyllithium; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00008a044