(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

Base Information

Chemical Name:(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
CAS No.:336625-21-9
Molecular Formula:C₁₈H₁₈F₃IO₅
Molecular Weight:498.238
Hs Code.:

Synonyms:(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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (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

Chemical Property:

Purity/Quality:: 98% HPLC ^*data from raw suppliers

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Technology Process of (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

There total 6 articles about (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 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: 77.0%

: 336625-20-8
Benzoic acid (3aR,4R,5R,6aS)-4-[(E)-3-hydroxy-4-(2-iodo-5-trifluoromethyl-phenoxy)-but-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

: 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

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃; for 2h;
DOI:10.1002/jlcr.441

Reference yield:

: 98-17-9
3-Trifluoromethylphenol

: 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

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 5 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

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