2,2-bis(hydroxymethyl)propyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-4-[3-(trifluoromethyl)-phenoxy]-1-butenyl]cyclopentyl]-5-heptenoate

Base Information

• Chemical Name: 2,2-bis(hydroxymethyl)propyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-4-[3-(trifluoromethyl)-phenoxy]-1-butenyl]cyclopentyl]-5-heptenoate
• CAS No.: 1420791-05-4
• Molecular Formula: C₂₈H₃₉F₃O₈
• Molecular Weight: 560.608

Synonyms:

Chemical Property of 2,2-bis(hydroxymethyl)propyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-4-[3-(trifluoromethyl)-phenoxy]-1-butenyl]cyclopentyl]-5-heptenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-bis(hydroxymethyl)propyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-4-[3-(trifluoromethyl)-phenoxy]-1-butenyl]cyclopentyl]-5-heptenoate

There total 10 articles about 2,2-bis(hydroxymethyl)propyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-4-[3-(trifluoromethyl)-phenoxy]-1-butenyl]cyclopentyl]-5-heptenoate 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:

3-Trifluoromethylphenol (98-17-9) → 2,2-bis(hydroxymethyl)propyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-4-[3-(trifluoromethyl)-phenoxy]-1-butenyl]cyclopentyl]-5-heptenoate (1420791-05-4) + 2,2-bis(hydroxymethyl)propyl (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-4-[3-(trifluoromethyl)-phenoxy]-1-butenyl]cyclopentyl]-5-heptenoate

Guidance literature:

Multi-step reaction with 9 steps

1.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 1.5 h / 90 - 100 °C

2.1: hydrogenchloride; water / acetone / 1 h / 70 °C

3.1: pyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

4.1: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 0 - 20 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane; toluene / 2.5 h / -78 - -20 °C / Inert atmosphere

6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C

7.1: lithium diisopropyl amide / tetrahydrofuran; hexane / -78 - -40 °C / Inert atmosphere

7.2: 1 h / -40 °C / Inert atmosphere

8.1: 20% sodium on mercury; methanol; disodium hydrogenphosphate / 5.5 h / 0 - 20 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 65 - 70 °C / Inert atmosphere

9.2: 0.25 h

With pyridine; 1H-imidazole; hydrogenchloride; methanol; disodium hydrogenphosphate; di-isopropyl azodicarboxylate; 20% sodium on mercury; tetrabutyl ammonium fluoride; water; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1.1: |Mitsunobu Displacement / 6.1: |Dess-Martin Oxidation / 8.1: |Julia-Lythgoe Olefination;

DOI:10.1016/j.tet.2012.11.087

Reference yield:

(R)-(-)-2,2-dimethyl-4-(3-trifluoromethylphenoxy)methyl-1,3-dioxolane → 2,2-bis(hydroxymethyl)propyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-4-[3-(trifluoromethyl)-phenoxy]-1-butenyl]cyclopentyl]-5-heptenoate (1420791-05-4) + 2,2-bis(hydroxymethyl)propyl (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-4-[3-(trifluoromethyl)-phenoxy]-1-butenyl]cyclopentyl]-5-heptenoate

Guidance literature:

Multi-step reaction with 8 steps

1.1: hydrogenchloride; water / acetone / 1 h / 70 °C

2.1: pyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

3.1: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 0 - 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / dichloromethane; toluene / 2.5 h / -78 - -20 °C / Inert atmosphere

5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C

6.1: lithium diisopropyl amide / tetrahydrofuran; hexane / -78 - -40 °C / Inert atmosphere

6.2: 1 h / -40 °C / Inert atmosphere

7.1: 20% sodium on mercury; methanol; disodium hydrogenphosphate / 5.5 h / 0 - 20 °C / Inert atmosphere

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 65 - 70 °C / Inert atmosphere

8.2: 0.25 h

With pyridine; 1H-imidazole; hydrogenchloride; methanol; disodium hydrogenphosphate; 20% sodium on mercury; tetrabutyl ammonium fluoride; water; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 5.1: |Dess-Martin Oxidation / 7.1: |Julia-Lythgoe Olefination;

DOI:10.1016/j.tet.2012.11.087

Reference yield:

(R)-(-)-2-hydroxy-3-(3-trifluoromethylphenoxy)propyl pivalate (1420790-91-5) → 2,2-bis(hydroxymethyl)propyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-4-[3-(trifluoromethyl)-phenoxy]-1-butenyl]cyclopentyl]-5-heptenoate (1420791-05-4) + 2,2-bis(hydroxymethyl)propyl (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-4-[3-(trifluoromethyl)-phenoxy]-1-butenyl]cyclopentyl]-5-heptenoate

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 0 - 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 2.5 h / -78 - -20 °C / Inert atmosphere

3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C

4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / -78 - -40 °C / Inert atmosphere

4.2: 1 h / -40 °C / Inert atmosphere

5.1: 20% sodium on mercury; methanol; disodium hydrogenphosphate / 5.5 h / 0 - 20 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 65 - 70 °C / Inert atmosphere

6.2: 0.25 h

With 1H-imidazole; methanol; disodium hydrogenphosphate; 20% sodium on mercury; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 3.1: |Dess-Martin Oxidation / 5.1: |Julia-Lythgoe Olefination;

DOI:10.1016/j.tet.2012.11.087

upstream raw materials:

3-Trifluoromethylphenol

(R)-(-)-2-hydroxy-3-(3-trifluoromethylphenoxy)propyl pivalate

(R)-(+)-2-(tert-butyldimethylsilyloxy)-3-(3-trifluoromethylphenoxy)propyl pivalate

(S)-(+)-2-(tert-butyldimethylsilyloxy)-3-(3-trifluoromethylphenoxy)propan-1-ol

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