(S,S)-15,16-dihydroxy-octadeca-9(Z),12(Z)-dienoic acid

Base Information

• Chemical Name: (S,S)-15,16-dihydroxy-octadeca-9(Z),12(Z)-dienoic acid
• CAS No.: 439242-00-9
• Molecular Formula: C₁₈H₃₂O₄
• Molecular Weight: 312.45
• Mol file: 439242-00-9.mol

Synonyms:

Chemical Property of (S,S)-15,16-dihydroxy-octadeca-9(Z),12(Z)-dienoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,S)-15,16-dihydroxy-octadeca-9(Z),12(Z)-dienoic acid

There total 12 articles about (S,S)-15,16-dihydroxy-octadeca-9(Z),12(Z)-dienoic 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: 99.0%

(9Z,12Z)-(15S,16S)-15,16-Dihydroxy-octadeca-9,12-dienoic acid methyl ester (439242-34-9) → (S,S)-15,16-dihydroxy-octadeca-9(Z),12(Z)-dienoic acid (439242-00-9)

Guidance literature:

With lithium hydroxide; In 1,2-dimethoxyethane; for 0.5h;

DOI:10.1016/S0040-4039(02)00117-X

Reference yield:

(E)-1-bromo-2-pentene (7348-71-2) → (S,S)-15,16-dihydroxy-octadeca-9(Z),12(Z)-dienoic acid (439242-00-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 86 percent / CsCO₃; CuI; NaI / dimethylformamide / 20 h

2: AD-mix-α; methanesulfonamide; aq. t-BuOH / 20 h / 0 °C

3: 99 percent / PPTS / 24 h

4: 85 percent / diisobutylaluminium hydride / diethyl ether / 3 h / 0 °C

5: 85 percent / CBr₄; PPh₃ / CH₂Cl₂ / 20 h / 0 °C

6: 86 percent / Cs₂CO₃; CuI; NaI / dimethylformamide / 20 h

7: 85 percent / pyridinium p-toluenesulfonate / methanol / 10 h / 50 °C

8: 95 percent / hydrogen; quinoline / Pd/BaSO₄ / methanol / 3 h

9: 99 percent / aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h

With quinoline; lithium hydroxide; AD-mix-α; copper(l) iodide; carbon tetrabromide; methanesulfonamide; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; caesium carbonate; triphenylphosphine; sodium iodide; tert-butyl alcohol; Pd-BaSO₄; In methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 2: Sharpless asymmetric dihydroxylation;

DOI:10.1016/S0040-4039(02)00117-X

Reference yield:

dec-9-ynoic acid (1642-49-5) → (S,S)-15,16-dihydroxy-octadeca-9(Z),12(Z)-dienoic acid (439242-00-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / H₂SO₄ / 20 h / 70 °C

2: 86 percent / Cs₂CO₃; CuI; NaI / dimethylformamide / 20 h

3: 85 percent / pyridinium p-toluenesulfonate / methanol / 10 h / 50 °C

4: 95 percent / hydrogen; quinoline / Pd/BaSO₄ / methanol / 3 h

5: 99 percent / aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h

With quinoline; lithium hydroxide; copper(l) iodide; sulfuric acid; hydrogen; pyridinium p-toluenesulfonate; caesium carbonate; sodium iodide; Pd-BaSO₄; In methanol; 1,2-dimethoxyethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(02)00117-X

upstream raw materials:

(9Z,12Z)-(15S,16S)-15,16-Dihydroxy-octadeca-9,12-dienoic acid methyl ester

(E)-1-bromo-2-pentene

dec-9-ynoic acid

methyl dec-9-ynoate