(3aR,4R,5R,6aS)-4-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol

Base Information

Chemical Name:(3aR,4R,5R,6aS)-4-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol
CAS No.:324763-89-5
Molecular Formula:C₂₇H₃₇ClO₇
Molecular Weight:509.04
Hs Code.:

(3aR,4R,5R,6aS)-4-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol

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Chemical Property of (3aR,4R,5R,6aS)-4-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol

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Technology Process of (3aR,4R,5R,6aS)-4-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol

There total 3 articles about (3aR,4R,5R,6aS)-4-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-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:

: 101915-58-6
(3aR,4R,5R,6aS)-4-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one

: 324763-89-5
(3aR,4R,5R,6aS)-4-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; toluene; for 0.333333h; Yield given;
DOI:10.1021/jm00143a018

Reference yield:

: 40665-94-9
dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate

: 324763-89-5
(3aR,4R,5R,6aS)-4-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) NaH / 1.) THF, 90 min, 2.) THF, 30 min

2: lithium triethylborohydride / tetrahydrofuran / 0.5 h

3: potassium carbonate / methanol; tetrahydrofuran / 2.5 h

4: p-toluenesulfonic acid / CH₂Cl₂ / 0.5 h

5: diisobutylaluminum hydride / toluene; hexane / 0.33 h

With sodium hydride; diisobutylaluminium hydride; lithium triethylborohydride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene;
DOI:10.1021/jm00143a018

Reference yield:

: 54324-79-7
(3aR,4R,5R,6aS)-4-((E)-4-(3-chlorophenoxy)-3-oxobut-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1′-biphenyl]-4-carboxylate

: 324763-89-5
(3aR,4R,5R,6aS)-4-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol

Guidance literature:: Multi-step reaction with 4 steps

1: lithium triethylborohydride / tetrahydrofuran / 0.5 h

2: potassium carbonate / methanol; tetrahydrofuran / 2.5 h

3: p-toluenesulfonic acid / CH₂Cl₂ / 0.5 h

4: diisobutylaluminum hydride / toluene; hexane / 0.33 h

With diisobutylaluminium hydride; lithium triethylborohydride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene;
DOI:10.1021/jm00143a018