(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-ol

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-ol
CAS No.:337529-29-0
Molecular Formula:C₂₈H₃₆F₃IO₇
Molecular Weight:668.489
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-ol

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-ol

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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-ol

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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-ol

There total 8 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-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: 85.0%

: 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

: 337529-29-0
(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-ol

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 ℃; for 1h;
DOI:10.1002/jlcr.441

Reference yield:

: 98-17-9
3-Trifluoromethylphenol

: 337529-29-0
(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-ol

Guidance literature:: Multi-step reaction with 8 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

8.1: 85 percent / DIBAL-H / tetrahydrofuran; toluene / 1 h / -78 °C

With n-butyllithium; sodium hydride; diisobutylaluminium 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

: 337529-29-0
(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-ol

Guidance literature:: Multi-step reaction with 7 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

7.1: 85 percent / DIBAL-H / tetrahydrofuran; toluene / 1 h / -78 °C

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