(3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-hexahydro-cyclopenta[b]furan-2-one

Base Information

Chemical Name:(3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-hexahydro-cyclopenta[b]furan-2-one
CAS No.:294856-06-7
Molecular Formula:C₂₉H₃₇F₃O₆
Molecular Weight:538.604
Hs Code.:

(3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-hexahydro-cyclopenta[b]furan-2-one

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Chemical Property of (3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-hexahydro-cyclopenta[b]furan-2-one

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Technology Process of (3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-hexahydro-cyclopenta[b]furan-2-one

There total 7 articles about (3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-hexahydro-cyclopenta[b]furan-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:

: 779-89-5,67801-07-4
3-(trifluoromethyl)cinnamic acid

: 294856-06-7
(3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-hexahydro-cyclopenta[b]furan-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: H₂ / 5 percent Pd/C / ethyl acetate

2.1: MeOH

3.1: N-BuLi / tetrahydrofuran / 0 °C

3.2: 80 percent / tetrahydrofuran

4.1: NaHMDS / 1,2-dimethoxy-ethane

4.2: 50 percent / 1,2-dimethoxy-ethane

5.1: (S)-BINAL-H; LiAlH₄ / tetrahydrofuran

6.1: K₂CO₃; MeOH

7.1: p-TSA / CH₂Cl₂

With methanol; lithium aluminium tetrahydride; n-butyllithium; (-)-(S)-BINAL-H; hydrogen; sodium hexamethyldisilazane; potassium carbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; ethyl acetate; 1.1: Catalytic hydrogenation / 2.1: Esterification / 3.1: Metallation / 3.2: Condensation / 4.1: Metallation / 4.2: Condensation / 5.1: Reduction / 6.1: deprotection / 7.1: Etherification;
DOI:10.1016/S0960-894X(00)00273-0

Reference yield:

: 70783-99-2
dimethyl 4-(3-trifluoromethylphenyl)-2-oxobutylphosphonate

: 294856-06-7
(3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-hexahydro-cyclopenta[b]furan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaHMDS / 1,2-dimethoxy-ethane

1.2: 50 percent / 1,2-dimethoxy-ethane

2.1: (S)-BINAL-H; LiAlH₄ / tetrahydrofuran

3.1: K₂CO₃; MeOH

4.1: p-TSA / CH₂Cl₂

With methanol; lithium aluminium tetrahydride; (-)-(S)-BINAL-H; sodium hexamethyldisilazane; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; 1.1: Metallation / 1.2: Condensation / 2.1: Reduction / 3.1: deprotection / 4.1: Etherification;
DOI:10.1016/S0960-894X(00)00273-0

Reference yield:

: 585-50-2
3-(3-trifluoromethylphenyl)propanoic acid

: 294856-06-7
(3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-5-(3-trifluoromethyl-phenyl)-pent-1-enyl]-hexahydro-cyclopenta[b]furan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: MeOH

2.1: N-BuLi / tetrahydrofuran / 0 °C

2.2: 80 percent / tetrahydrofuran

3.1: NaHMDS / 1,2-dimethoxy-ethane

3.2: 50 percent / 1,2-dimethoxy-ethane

4.1: (S)-BINAL-H; LiAlH₄ / tetrahydrofuran

5.1: K₂CO₃; MeOH

6.1: p-TSA / CH₂Cl₂

With methanol; lithium aluminium tetrahydride; n-butyllithium; (-)-(S)-BINAL-H; sodium hexamethyldisilazane; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; 1.1: Esterification / 2.1: Metallation / 2.2: Condensation / 3.1: Metallation / 3.2: Condensation / 4.1: Reduction / 5.1: deprotection / 6.1: Etherification;
DOI:10.1016/S0960-894X(00)00273-0