(5Z,10E)-(8RS,12R)-8-acetyl-12-cyclohexyl-12-hydroxy-5,10-dodecadienoic acid

Base Information

• Chemical Name: (5Z,10E)-(8RS,12R)-8-acetyl-12-cyclohexyl-12-hydroxy-5,10-dodecadienoic acid
• CAS No.: 80078-25-7
• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.472
• Mol file: 80078-25-7.mol

Synonyms:

Chemical Property of (5Z,10E)-(8RS,12R)-8-acetyl-12-cyclohexyl-12-hydroxy-5,10-dodecadienoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5Z,10E)-(8RS,12R)-8-acetyl-12-cyclohexyl-12-hydroxy-5,10-dodecadienoic acid

There total 10 articles about (5Z,10E)-(8RS,12R)-8-acetyl-12-cyclohexyl-12-hydroxy-5,10-dodecadienoic 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: 84.3%

methyl (5Z,10E)-(8RS,12S)-8-acetyl-12-cyclohexyl-12-hydroxy-5,10-dodecadienoate (80078-24-6,80125-02-6,82510-42-7,82510-43-8,82510-44-9,82534-89-2) → (5Z,10E)-(8RS,12S)-8-acetyl-12-cyclohexyl-12-hydroxy-5,10-dodecadienoic acid (80078-25-7,80126-80-3,80513-39-9,80513-70-8,82510-24-5,82510-45-0)

Guidance literature:

With sodium hydroxide; In methanol; for 12h; Ambient temperature;

DOI:10.1248/cpb.30.51

Reference yield: 74.4%

methyl (5Z,10E)-(8RS,12R)-8-acetyl-12-cyclohexyl-12-hydroxy-5,10-dodecadienoate (80078-24-6,80125-02-6,82510-42-7,82510-43-8,82510-44-9,82534-89-2) → (5Z,10E)-(8RS,12R)-8-acetyl-12-cyclohexyl-12-hydroxy-5,10-dodecadienoic acid (80078-25-7,80126-80-3,80513-39-9,80513-70-8,82510-24-5,82510-45-0)

Guidance literature:

With sodium hydroxide; In methanol; for 12h; Ambient temperature;

DOI:10.1248/cpb.30.51

Reference yield:

methyl (5Z)-7-iodo-5-heptenoate (64493-06-7) → (5Z,10E)-(8RS,12S)-8-acetyl-12-cyclohexyl-12-hydroxy-5,10-dodecadienoic acid (80078-25-7,80126-80-3,80513-39-9,80513-70-8,82510-24-5,82510-45-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 18.4 percent / n-BuLi, diisopropylamine / tetrahydrofuran; hexane / -20 deg C, 20 min. then room temp., 1 h

2: 68.2 percent / acetic acid / H₂O; tetrahydrofuran / 18 h / Ambient temperature

3: 84.3 percent / 1 N NaOH / methanol / 12 h / Ambient temperature

With sodium hydroxide; n-butyllithium; acetic acid; diisopropylamine; In tetrahydrofuran; methanol; hexane; water;

DOI:10.1248/cpb.30.51

upstream raw materials:

methyl (5Z,10E)-(8RS,12S)-8-acetyl-12-cyclohexyl-12-hydroxy-5,10-dodecadienoate

methyl (5Z)-7-iodo-5-heptenoate

(1E)-(3S)-3-tert-butyldimethylsilyloxy-3-cyclohexyl-1-iodo-1-propene

(5E)-(7S)-7-tert-butyldimethylsilyloxy-7-cyclohexyl-5-hepten-2-one