(Z)-3-Bromo-4-[(1S,2R,3aS,6aS)-5-[2-methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-1-phenoxy-but-3-en-2-one

Base Information

Chemical Name:(Z)-3-Bromo-4-[(1S,2R,3aS,6aS)-5-[2-methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-1-phenoxy-but-3-en-2-one
CAS No.:120294-29-3
Molecular Formula:C₂₆H₃₃BrO₅
Molecular Weight:505.449
Hs Code.:

Synonyms:(Z)-3-Bromo-4-[(1S,2R,3aS,6aS)-5-[2-methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-1-phenoxy-but-3-en-2-one

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Chemical Property of (Z)-3-Bromo-4-[(1S,2R,3aS,6aS)-5-[2-methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-1-phenoxy-but-3-en-2-one

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Technology Process of (Z)-3-Bromo-4-[(1S,2R,3aS,6aS)-5-[2-methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-1-phenoxy-but-3-en-2-one

There total 10 articles about (Z)-3-Bromo-4-[(1S,2R,3aS,6aS)-5-[2-methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-1-phenoxy-but-3-en-2-one 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:

: 112741-26-1
3-Bromo-4-hydroxy-4-[(1S,2R,3aS,6aS)-5-[2-methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-1-phenoxy-butan-2-one

: 112741-39-6
(E)-4-[(1R,2R,3aS,6aS)-5-[2-Methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-1-phenoxy-but-3-en-2-one

: 120294-29-3
(Z)-3-Bromo-4-[(1S,2R,3aS,6aS)-5-[2-methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-1-phenoxy-but-3-en-2-one

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

Reference yield:

: 2065-23-8
methyl 2-phenoxyacetate

: 120294-29-3
(Z)-3-Bromo-4-[(1S,2R,3aS,6aS)-5-[2-methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-1-phenoxy-but-3-en-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) LDA / 1.) ether, THF, -100 deg C, 15 min, 2.) from -100 deg C to -60 deg C, 2.5 h

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

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

With diethylaluminium chloride; methanesulfonyl chloride; triethylamine; copper(I) bromide; zinc; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;
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

: 120294-29-3
(Z)-3-Bromo-4-[(1S,2R,3aS,6aS)-5-[2-methoxy-eth-(E)-ylidene]-2-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl]-1-phenoxy-but-3-en-2-one

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