(2E,10R)-10-(Benzyloxy)undec-2-en-7-yn-1-ol

Base Information

• Chemical Name: (2E,10R)-10-(Benzyloxy)undec-2-en-7-yn-1-ol
• CAS No.: 124887-04-3
• Molecular Formula: C₁₈H₂₄O₂
• Molecular Weight: 272.387
• Mol file: 124887-04-3.mol

Synonyms:(2E,10R)-10-(Benzyloxy)undec-2-en-7-yn-1-ol

Chemical Property of (2E,10R)-10-(Benzyloxy)undec-2-en-7-yn-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,10R)-10-(Benzyloxy)undec-2-en-7-yn-1-ol

There total 9 articles about (2E,10R)-10-(Benzyloxy)undec-2-en-7-yn-1-ol 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: 80.0%

Ethyl (2E,10R)-10-(benzyloxy)undec-2-en-7-ynoate (152896-82-7) → (2E,10R)-10-(Benzyloxy)undec-2-en-7-yn-1-ol (124887-04-3)

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; at 0 ℃; for 2.5h;

DOI:10.1021/jo00077a047

Reference yield:

2-(hex-5-yn-1-yloxy)tetrahydro-2H-pyran (1720-37-2) → (2E,10R)-10-(Benzyloxy)undec-2-en-7-yn-1-ol (124887-04-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 65 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1.) 0 deg C, 45 min, 2.) room temp., overnight

2: 68 percent / NaH, n-Bu₄NI / tetrahydrofuran

3: p-TsOH / methanol / 2 h

4: 1.) (COCl)2, DMSO, 2.) Et₃N / CH₂Cl₂ / 1.) -78 deg C, 20 min, 2.) -78 deg C to room temp.

5: 75 percent / LiCl, i-Pr₂NEt / acetonitrile / 1.) 15 min, room temp., 2.) room temp., overnight

6: 80 percent / DIBALH / diethyl ether / 2.5 h / 0 °C

With n-butyllithium; oxalyl dichloride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; acetonitrile;

DOI:10.1021/jo00077a047

Reference yield:

benzyl bromide (100-39-0) → (2E,10R)-10-(Benzyloxy)undec-2-en-7-yn-1-ol (124887-04-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / NaH, n-Bu₄NI / tetrahydrofuran

2: p-TsOH / methanol / 2 h

3: 1.) (COCl)2, DMSO, 2.) Et₃N / CH₂Cl₂ / 1.) -78 deg C, 20 min, 2.) -78 deg C to room temp.

4: 75 percent / LiCl, i-Pr₂NEt / acetonitrile / 1.) 15 min, room temp., 2.) room temp., overnight

5: 80 percent / DIBALH / diethyl ether / 2.5 h / 0 °C

With oxalyl dichloride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/jo00077a047

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

Ethyl (2E,10R)-10-(benzyloxy)undec-2-en-7-ynoate

2-(hex-5-yn-1-yloxy)tetrahydro-2H-pyran

benzyl bromide

Downstream raw materials:

(2S,3S,10R)-10-(Benzyloxy)-2,3-epoxy-7-undecyn-1-ol

(5S,12R)-5-hydroxyy-12-methyl-1-oxa-3-cyclododecen-2-one

(2R,9S,10S)-2-(Benzyloxy)-9,10-epoxy-11-(tert-butyldimethylsiloxy)-4-undecyne

Refernces

• 1、 Leemhuis,Thijs,Zwanenburg. "Total synthesis of patulolide C and its homo, nor, and iso analogs". . p. 7170 - 7179. Retrieved 2007/10/02.