(Z)-2-Bromo-1-cyclohexyl-3-[(1S,2R,3aS,6aS)-5-[2-methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-propenone

Base Information

Chemical Name:(Z)-2-Bromo-1-cyclohexyl-3-[(1S,2R,3aS,6aS)-5-[2-methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-propenone
CAS No.:120294-28-2
Molecular Formula:C₂₅H₃₇BrO₄
Molecular Weight:481.47
Hs Code.:

Synonyms:(Z)-2-Bromo-1-cyclohexyl-3-[(1S,2R,3aS,6aS)-5-[2-methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-propenone

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Chemical Property of (Z)-2-Bromo-1-cyclohexyl-3-[(1S,2R,3aS,6aS)-5-[2-methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-propenone

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Technology Process of (Z)-2-Bromo-1-cyclohexyl-3-[(1S,2R,3aS,6aS)-5-[2-methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-propenone

There total 9 articles about (Z)-2-Bromo-1-cyclohexyl-3-[(1S,2R,3aS,6aS)-5-[2-methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-propenone 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:

: 112741-25-0
2-Bromo-1-cyclohexyl-3-hydroxy-3-[(1S,2R,3aS,6aS)-5-[2-methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-propan-1-one

: 112741-38-5
(E)-1-Cyclohexyl-3-[(1R,2R,3aS,6aS)-5-[2-methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-propenone

: 120294-28-2
(Z)-2-Bromo-1-cyclohexyl-3-[(1S,2R,3aS,6aS)-5-[2-methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-propenone

Guidance literature:: With methanesulfonyl chloride; triethylamine; In dichloromethane; at 10 ℃; for 10h; Yields of byproduct given;
DOI:10.1021/jo00241a020

Reference yield:

: 112741-21-6
(1R,2R,3aS,6aS)-5-[2-Methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalene-1-carbaldehyde

: 120294-28-2
(Z)-2-Bromo-1-cyclohexyl-3-[(1S,2R,3aS,6aS)-5-[2-methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-propenone

Guidance literature:: Multi-step reaction with 2 steps

1: diethylaluminium chloride, Zn, CuBr / tetrahydrofuran; hexane / 1 h / -5 °C

2: methanesulfonyl chloride, Et₃N / CH₂Cl₂ / 10 h / 10 °C

With diethylaluminium chloride; methanesulfonyl chloride; triethylamine; copper(I) bromide; zinc; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo00241a020

Reference yield:

: 92134-25-3
(1R,5S,6S,7R)-6-tert-butyldimethylsilyloxymethyl-7-tetrahydropyranyloxybicyclo<3.3.0>oct-2-ene-3-carbaldehyde

: 120294-28-2
(Z)-2-Bromo-1-cyclohexyl-3-[(1S,2R,3aS,6aS)-5-[2-methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-propenone

Guidance literature:: Multi-step reaction with 6 steps

1: LDA / toluene; tetrahydrofuran / 0 °C

2: MBZ*Cr(CO)3, H₂ / acetone / 120 °C

3: tetrabutylamonium fluoride (TBAF) / tetrahydrofuran / Ambient temperature

4: SO₃*pyridine complex, Et₃N / dimethylsulfoxide / Ambient temperature

5: diethylaluminium chloride, Zn, CuBr / tetrahydrofuran; hexane / 1 h / -5 °C

6: methanesulfonyl chloride, Et₃N / CH₂Cl₂ / 10 h / 10 °C

With pyridine-SO₃ complex; MBZ*Cr(CO)3; tetrabutyl ammonium fluoride; hydrogen; diethylaluminium chloride; methanesulfonyl chloride; triethylamine; copper(I) bromide; zinc; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; acetone; toluene;
DOI:10.1021/jo00241a020