(Z)-7-((1R,2R,3R,5S)-3-[(tert-butyldimethylsilanyl)oxy]-2-{(S,E)-3-[(tert-butyldimethylsilanyl)oxy]oct-1-en-1-yl}-5-hydroxycyclopentyl)hept-5-enoic acid

Base Information

• Chemical Name: (Z)-7-((1R,2R,3R,5S)-3-[(tert-butyldimethylsilanyl)oxy]-2-{(S,E)-3-[(tert-butyldimethylsilanyl)oxy]oct-1-en-1-yl}-5-hydroxycyclopentyl)hept-5-enoic acid
• CAS No.: 1239683-12-5
• Molecular Formula: C₃₂H₆₂O₅Si₂
• Molecular Weight: 583.012
• Mol file: 1239683-12-5.mol

Synonyms:(Z)-7-((1R,2R,3R,5S)-3-[(tert-butyldimethylsilanyl)oxy]-2-{(S,E)-3-[(tert-butyldimethylsilanyl)oxy]oct-1-en-1-yl}-5-hydroxycyclopentyl)hept-5-enoic acid

Chemical Property of (Z)-7-((1R,2R,3R,5S)-3-[(tert-butyldimethylsilanyl)oxy]-2-{(S,E)-3-[(tert-butyldimethylsilanyl)oxy]oct-1-en-1-yl}-5-hydroxycyclopentyl)hept-5-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-7-((1R,2R,3R,5S)-3-[(tert-butyldimethylsilanyl)oxy]-2-{(S,E)-3-[(tert-butyldimethylsilanyl)oxy]oct-1-en-1-yl}-5-hydroxycyclopentyl)hept-5-enoic acid

There total 1 articles about (Z)-7-((1R,2R,3R,5S)-3-[(tert-butyldimethylsilanyl)oxy]-2-{(S,E)-3-[(tert-butyldimethylsilanyl)oxy]oct-1-en-1-yl}-5-hydroxycyclopentyl)hept-5-enoic acid 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:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → (Z)-7-((1R,2R,3R,5S)-3-[(tert-butyldimethylsilanyl)oxy]-2-{(S,E)-3-[(tert-butyldimethylsilanyl)oxy]oct-1-en-1-yl}-5-hydroxycyclopentyl)hept-5-enoic acid (1239683-12-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: formic acid; sulfuric acid / 24 h / 80 °C

1.2: 2 h / 0 - 20 °C

2.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane; N,N-dimethyl acetamide / 6 h / 20 °C

3.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

3.2: 6 h / 0 - 20 °C / Inert atmosphere

4.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / tetrahydrofuran; toluene / 1 h / -30 °C

5.1: 1H-imidazole / dichloromethane / 18 h / 20 °C

6.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C

7.1: potassium hexamethylsilazane / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere

7.2: 4 h / -20 - -10 °C / Inert atmosphere

With 1H-imidazole; formic acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; dimethylsulfide borane complex; sulfuric acid; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; toluene; 3.1: |Horner-Wadsworth-Emmons Olefination / 3.2: |Horner-Wadsworth-Emmons Olefination / 4.1: |Corey-Bakshi-Shibata Reduction;

DOI:10.1002/anie.201902371

Reference yield: 90.0%

(Z)-7-((1R,2R,3R,5S)-3-[(tert-butyldimethylsilanyl)oxy]-2-{(S,E)-3-[(tert-butyldimethylsilanyl)oxy]oct-1-en-1-yl}-5-hydroxycyclopentyl)hept-5-enoic acid (1239683-12-5) → dinoprost (551-11-1)

Guidance literature:

With hydrogen fluoride; water; In acetonitrile; at 20 ℃; for 7h; stereoselective reaction;

DOI:10.1016/j.tet.2010.07.069

Reference yield:

(Z)-7-((1R,2R,3R,5S)-3-[(tert-butyldimethylsilanyl)oxy]-2-{(S,E)-3-[(tert-butyldimethylsilanyl)oxy]oct-1-en-1-yl}-5-hydroxycyclopentyl)hept-5-enoic acid (1239683-12-5) → dinoprostone (363-24-6)

Guidance literature:

Multi-step reaction with 2 steps

1: Dess-Martin periodane / dichloromethane / 20 °C

2: pyridine hydrogenfluoride / acetonitrile; water / 4 h / 0 - 20 °C

With Dess-Martin periodane; pyridine hydrogenfluoride; In dichloromethane; water; acetonitrile;

DOI:10.1002/anie.201902371

upstream raw materials:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one

Downstream raw materials:

dinoprost

dinoprostone

prostaglandin A₂

Refernces