2,2-bis(hydroxymethyl)propyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]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-5-phenyl-1-pentenyl]cyclopentyl]-5-heptenoate
• CAS No.: 1430731-70-6
• Molecular Formula: C₂₈H₄₂O₇
• Molecular Weight: 490.637
• Mol file: 1430731-70-6.mol

Synonyms:2,2-bis(hydroxymethyl)propyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-heptenoate

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

Chemical Property:

Purity/Quality:

98% HPLC ^*data from raw suppliers

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-5-phenyl-1-pentenyl]cyclopentyl]-5-heptenoate

There total 11 articles about 2,2-bis(hydroxymethyl)propyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]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:

1-[(4Z)-6-[(1R,2R,3R,5S)-2-[(1E,3S)-3-(tert-buthyldimethylsilyloxy)-5-phenyl-1-pentenyl]-3,5-bis(triethylsilyloxy)cydopentyl]-4-hexenyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octan → 2,2-bis(hydroxymethyl)propyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-heptenoate (1430731-70-6)

Guidance literature:

1-[(4Z)-6-[(1R,2R,3R,5S)-2-[(1E,3S)-3-(tert-buthyldimethylsilyloxy)-5-phenyl-1-pentenyl]-3,5-bis(triethylsilyloxy)cydopentyl]-4-hexenyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octan; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 60 ℃; for 2h;

With citric acid; In water; for 0.25h;

Reference yield:

C28H40O6 → 2,2-bis(hydroxymethyl)propyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-heptenoate (1430731-70-6) + 2,2-bis(hydroxymethyl)propyl (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-heptenoate (955005-79-5)

Guidance literature:

With citric acid; In water; for 0.25h; Overall yield = 16.42 g;

Reference yield:

(S)-4-phenyl-1,2-butanediol (124988-64-3) → 2,2-bis(hydroxymethyl)propyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-heptenoate (1430731-70-6) + 2,2-bis(hydroxymethyl)propyl (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-heptenoate (955005-79-5)

Guidance literature:

Multi-step reaction with 8 steps

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

2.1: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 0 - 20 °C / Inert atmosphere

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

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

5.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -60 °C / Inert atmosphere

5.2: 0.33 h / Cooling

6.1: disodium hydrogenphosphate; sodium amalgam; methanol / 20 h

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 60 °C

8.1: citric acid / water / 0.25 h

With pyridine; 1H-imidazole; methanol; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; diisopropylamine; citric acid; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

upstream raw materials:

(S)-4-phenyl-1,2-butanediol

(S)-(-)-2-hydroxy-4-phenylbutyl pivalate

(S)-(+)-2-(tert-butyldimethylsilyloxy)-4-phenylbutyl pivalate

(S)-(-)-2-(tert-butyldimethylsilyloxy)-4-phenylbutan-1-ol

Downstream raw materials:

bimatoprost

Refernces

• 1、 -. "PROCESS FOR PREPARATION OF PROSTAGLANDIN F2α ANALOGUES". . . Retrieved 2013/09/26.