Hexadec-15-ynoic acid (S)-3-benzyloxy-2-(12-methoxy-dodecanoyloxy)-propyl ester

Base Information

• Chemical Name: Hexadec-15-ynoic acid (S)-3-benzyloxy-2-(12-methoxy-dodecanoyloxy)-propyl ester
• CAS No.: 183145-01-9
• Molecular Formula: C₃₉H₆₄O₆
• Molecular Weight: 628.934
• Mol file: 183145-01-9.mol

Synonyms:Hexadec-15-ynoic acid (S)-3-benzyloxy-2-(12-methoxy-dodecanoyloxy)-propyl ester

Chemical Property of Hexadec-15-ynoic acid (S)-3-benzyloxy-2-(12-methoxy-dodecanoyloxy)-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of Hexadec-15-ynoic acid (S)-3-benzyloxy-2-(12-methoxy-dodecanoyloxy)-propyl ester

There total 4 articles about Hexadec-15-ynoic acid (S)-3-benzyloxy-2-(12-methoxy-dodecanoyloxy)-propyl ester 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: 72.0%

12-(methoxy)dodecanoic acid (92169-28-3) + Hexadec-15-ynoic acid (S)-3-benzyloxy-2-hydroxy-propyl ester (183144-92-5) → Hexadec-15-ynoic acid (S)-3-benzyloxy-2-(12-methoxy-dodecanoyloxy)-propyl ester (183145-01-9)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; Ambient temperature;

DOI:10.1021/jo9605455

Reference yield:

12-hydroxydodecanoic acid (505-95-3) → Hexadec-15-ynoic acid (S)-3-benzyloxy-2-(12-methoxy-dodecanoyloxy)-propyl ester (183145-01-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1) THF, DMF, rt, overnight; 2) THF, DMF, reflux, overnight

2: 72 percent / DMAP, 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / Ambient temperature

With dmap; sodium hydride; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1021/jo9605455

Reference yield:

(R)-3-benzyloxy-1,2-propanediol (56552-80-8) → Hexadec-15-ynoic acid (S)-3-benzyloxy-2-(12-methoxy-dodecanoyloxy)-propyl ester (183145-01-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / DMAP, 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 20 °C

2: 72 percent / DMAP, 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / Ambient temperature

With dmap; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1021/jo9605455

upstream raw materials:

12-(methoxy)dodecanoic acid

Hexadec-15-ynoic acid (S)-3-benzyloxy-2-hydroxy-propyl ester

12-hydroxydodecanoic acid

(R)-3-benzyloxy-1,2-propanediol

Downstream raw materials:

Dotriaconta-15,17-diynedioic acid bis-[(S)-3-benzyloxy-2-(8-methoxy-octanoyloxy)-propyl] ester

Dotriaconta-15,17-diynedioic acid bis-[(S)-3-benzyloxy-2-(12-methoxy-dodecanoyloxy)-propyl] ester