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

Base Information

Chemical Name:(3aR,4R,5R,6aS)-4-[(E)-4-(2-Iodo-5-trifluoromethyl-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one
CAS No.:337529-28-9
Molecular Formula:C₂₈H₃₄F₃IO₇
Molecular Weight:666.473
Hs Code.:

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

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

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

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

There total 7 articles about (3aR,4R,5R,6aS)-4-[(E)-4-(2-Iodo-5-trifluoromethyl-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-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: 98.0%

: 110-87-2
3,4-dihydro-2H-pyran

: 336625-21-9
(3aR)(3aα,4β,5α,6aα)-5-hydroxy-4-[(E)-3-hydroxy-4-(2-iodo-5-trifluoromethylphenoxy)-but-1-enyl]-hexahydro-cyclopenta[b]furan-2-one

: 337529-28-9
(3aR,4R,5R,6aS)-4-[(E)-4-(2-Iodo-5-trifluoromethyl-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one

Guidance literature:: With toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1002/jlcr.441

Reference yield:

: 98-17-9
3-Trifluoromethylphenol

: 337529-28-9
(3aR,4R,5R,6aS)-4-[(E)-4-(2-Iodo-5-trifluoromethyl-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium hydride / toluene; various solvent(s) / 0.08 h

1.2: 86 percent / iodine / toluene; various solvent(s) / 16 h / 20 °C

2.1: 48 percent / potassium carbonate / acetone / 16 h / Heating

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: 22 percent / tetrahydrofuran; hexane / 2 h

4.1: 60 percent / LiCl; triethylamine / tetrahydrofuran / 3.33 h / 5 - 20 °C

5.1: 97 percent / (-)-chlorodiisopinocampheylborane / tetrahydrofuran / 20.5 h / -20 - 20 °C

6.1: 77 percent / potassium carbonate / methanol / 2 h / 20 °C

7.1: 98 percent / p-toluenesulfonic acid / CH₂Cl₂; tetrahydrofuran

With n-butyllithium; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; (-)-diisopinocamphenylborane chloride; lithium chloride; In tetrahydrofuran; methanol; hexane; dichloromethane; acetone; toluene;
DOI:10.1002/jlcr.441

Reference yield:

: 102771-00-6
2-iodo-5-(trifluoromethyl)phenol

: 337529-28-9
(3aR,4R,5R,6aS)-4-[(E)-4-(2-Iodo-5-trifluoromethyl-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 48 percent / potassium carbonate / acetone / 16 h / Heating

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 22 percent / tetrahydrofuran; hexane / 2 h

3.1: 60 percent / LiCl; triethylamine / tetrahydrofuran / 3.33 h / 5 - 20 °C

4.1: 97 percent / (-)-chlorodiisopinocampheylborane / tetrahydrofuran / 20.5 h / -20 - 20 °C

5.1: 77 percent / potassium carbonate / methanol / 2 h / 20 °C

6.1: 98 percent / p-toluenesulfonic acid / CH₂Cl₂; tetrahydrofuran

With n-butyllithium; potassium carbonate; toluene-4-sulfonic acid; triethylamine; (-)-diisopinocamphenylborane chloride; lithium chloride; In tetrahydrofuran; methanol; hexane; dichloromethane; acetone;
DOI:10.1002/jlcr.441