Threo-9,10-dihydroxy-12-trans-octadecensaeure

Base Information

• Chemical Name: Threo-9,10-dihydroxy-12-trans-octadecensaeure
• CAS No.: 125356-87-8
• Molecular Formula: C₁₈H₃₄O₄
• Molecular Weight: 314.466
• Mol file: 125356-87-8.mol

Synonyms:

Chemical Property of Threo-9,10-dihydroxy-12-trans-octadecensaeure

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Threo-9,10-dihydroxy-12-trans-octadecensaeure

There total 13 articles about Threo-9,10-dihydroxy-12-trans-octadecensaeure 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: 100.0%

methyl (Z)-(9S,10R)-9,10-dihydroxyoctadec-12-enoate → (Z)-(9S,10R)-9,10-dihydroxyoctadec-12-enoic acid (125356-87-8,263399-34-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃;

DOI:10.1021/acs.orglett.5b02814

Reference yield:

methyl 9-hydroxynonanoate (34957-73-8) → (Z)-(9S,10R)-9,10-dihydroxyoctadec-12-enoic acid (125356-87-8,263399-34-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C / Inert atmosphere; Molecular sieve

2.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.25 h / -78 - 0 °C / Inert atmosphere

2.2: -78 - 20 °C

3.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 12 h / 20 °C / Inert atmosphere

4.1: 5% Pd-CaCO3; quinoline; hydrogen / methanol / 3.5 h / 20 °C

5.1: lithium hydroxide / tetrahydrofuran; water / 0 - 20 °C

With quinoline; osmium(VIII) oxide; 5% Pd-CaCO3; hydrogen; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; pyridinium chlorochromate; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; tert-butyl alcohol;

DOI:10.1021/acs.orglett.5b02814

Reference yield:

1-iodonon-3-yne (85612-95-9) → (Z)-(9S,10R)-9,10-dihydroxyoctadec-12-enoic acid (125356-87-8,263399-34-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: toluene / 20 h / 80 °C / Inert atmosphere

2.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.25 h / -78 - 0 °C / Inert atmosphere

2.2: -78 - 20 °C

3.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 12 h / 20 °C / Inert atmosphere

4.1: 5% Pd-CaCO3; quinoline; hydrogen / methanol / 3.5 h / 20 °C

5.1: lithium hydroxide / tetrahydrofuran; water / 0 - 20 °C

With quinoline; osmium(VIII) oxide; 5% Pd-CaCO3; hydrogen; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; lithium hydroxide; In tetrahydrofuran; methanol; water; acetone; toluene; tert-butyl alcohol;

DOI:10.1021/acs.orglett.5b02814

upstream raw materials:

methyl 9-hydroxynonanoate

1-iodonon-3-yne

(3-nonyn-1-yl)triphenylphosphonium iodide

methyl cis-octadec-9-en-12-ynoate

Downstream raw materials:

erythro-9,10-dihydroxystearic acid