(5S,8E,10E,12R)-isopropyl 5,12-dihydroxypentadeca-8,10-dien-6,14-diynoate

Base Information

• Chemical Name: (5S,8E,10E,12R)-isopropyl 5,12-dihydroxypentadeca-8,10-dien-6,14-diynoate
• CAS No.: 1251537-11-7
• Molecular Formula: C₁₈H₂₄O₄
• Molecular Weight: 304.386
• Mol file: 1251537-11-7.mol

Synonyms:

Chemical Property of (5S,8E,10E,12R)-isopropyl 5,12-dihydroxypentadeca-8,10-dien-6,14-diynoate

Chemical Property:

• Boiling Point: 471.0±45.0 °C(Predicted)
• Density: 1.088±0.06 g/cm3(Predicted)

Purity/Quality:

98% ^*data from raw suppliers

(5S,8E,10E,12R)-5,12-Dihydroxy-8,10-pentadecadiene-6,14-diynoicAcid1-MethylethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (5S,8E,10E,12R)-5,12-Dihydroxy-8,10-pentadecadiene-6,14-diynoic Acid 1-Methylethyl Ester is an intermediate in the synthesis of Resolvin E1 (R144690), an omega-3 polyunsaturated fatty acid derivative that exhibits potent anti-inflammatory, pro-resolution, and anti-nociceptive effects.

Technology Process of (5S,8E,10E,12R)-isopropyl 5,12-dihydroxypentadeca-8,10-dien-6,14-diynoate

There total 6 articles about (5S,8E,10E,12R)-isopropyl 5,12-dihydroxypentadeca-8,10-dien-6,14-diynoate 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%

(5S,8E,10E,12R)-isopropyl 12-(tert-butyldiphenylsilyloxy)-5-hydroxy-15-(trimethylsilyl)pentadeca-8,10-dien-6,14-diynoate (1251537-19-5) → (5S,8E,10E,12R)-isopropyl 5,12-dihydroxypentadeca-8,10-dien-6,14-diynoate (1251537-11-7)

Guidance literature:

With tetrabutyl ammonium fluoride; ammonium chloride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2011.03.035

Reference yield:

glutaric anhydride, (108-55-4) → (5S,8E,10E,12R)-isopropyl 5,12-dihydroxypentadeca-8,10-dien-6,14-diynoate (1251537-11-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: aluminum (III) chloride / dichloromethane / -5 - 20 °C

2.1: toluene-4-sulfonic acid / 24 h / 65 °C

3.1: Noyori catalyst / isopropyl alcohol / 0.33 h / 20 °C

4.1: ammonium chloride / tetrahydrofuran / 0.25 h / 0 °C

4.2: 2 h / 20 °C

5.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diethylamine / 16 h / 20 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride; ammonium chloride / tetrahydrofuran / 2 h / 20 °C

With aluminum (III) chloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; ammonium chloride; toluene-4-sulfonic acid; diethylamine; In tetrahydrofuran; dichloromethane; isopropyl alcohol; 5.1: Sonogashira coupling;

DOI:10.1016/j.tetlet.2011.03.035

Reference yield:

C13H24O3Si (1251537-13-9) → (5S,8E,10E,12R)-isopropyl 5,12-dihydroxypentadeca-8,10-dien-6,14-diynoate (1251537-11-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: ammonium chloride / tetrahydrofuran / 0.25 h / 0 °C

1.2: 2 h / 20 °C

2.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diethylamine / 16 h / 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride; ammonium chloride / tetrahydrofuran / 2 h / 20 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; ammonium chloride; diethylamine; In tetrahydrofuran; 2.1: Sonogashira coupling;

DOI:10.1016/j.tetlet.2011.03.035

upstream raw materials:

glutaric anhydride,

(5S,8E,10E,12R)-isopropyl 12-(tert-butyldiphenylsilyloxy)-5-hydroxy-15-(trimethylsilyl)pentadeca-8,10-dien-6,14-diynoate

C₁₃H₂₄O₃Si

(S)-isopropyl 5-hydroxyhept-6-ynoate

Downstream raw materials:

Resolvin E₁