(3R,4E,7R,9S,10E)-7,9-di(benzyloxy)-11-phenyl-1-(tetrahydro-2H-2-pyranyloxy)-4,10-undecadien-3-ol

Base Information

• Chemical Name: (3R,4E,7R,9S,10E)-7,9-di(benzyloxy)-11-phenyl-1-(tetrahydro-2H-2-pyranyloxy)-4,10-undecadien-3-ol
• CAS No.: 1276622-05-9
• Molecular Formula: C₃₆H₄₄O₅
• Molecular Weight: 556.742
• Mol file: 1276622-05-9.mol

Synonyms:(3R,4E,7R,9S,10E)-7,9-di(benzyloxy)-11-phenyl-1-(tetrahydro-2H-2-pyranyloxy)-4,10-undecadien-3-ol

Chemical Property of (3R,4E,7R,9S,10E)-7,9-di(benzyloxy)-11-phenyl-1-(tetrahydro-2H-2-pyranyloxy)-4,10-undecadien-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4E,7R,9S,10E)-7,9-di(benzyloxy)-11-phenyl-1-(tetrahydro-2H-2-pyranyloxy)-4,10-undecadien-3-ol

There total 12 articles about (3R,4E,7R,9S,10E)-7,9-di(benzyloxy)-11-phenyl-1-(tetrahydro-2H-2-pyranyloxy)-4,10-undecadien-3-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: 87.0%

(3R,7R,9S,10E)-7,9-di(benzyloxy)-11-phenyl-1-(tetrahydro-2H-2-pyranyloxy)-10-undecen-4-yn-3-ol (1276622-02-6) → (3R,4E,7R,9S,10E)-7,9-di(benzyloxy)-11-phenyl-1-(tetrahydro-2H-2-pyranyloxy)-4,10-undecadien-3-ol (1276622-05-9)

Guidance literature:

(3R,7R,9S,10E)-7,9-di(benzyloxy)-11-phenyl-1-(tetrahydro-2H-2-pyranyloxy)-10-undecen-4-yn-3-ol; With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 39h; Inert atmosphere; Reflux;

With water; sodium sulfate; In tetrahydrofuran; at 0 ℃;

DOI:10.1002/cjoc.201190015

Reference yield:

(S)-(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-but-3-yn-2-ol (914638-76-9) → (3R,4E,7R,9S,10E)-7,9-di(benzyloxy)-11-phenyl-1-(tetrahydro-2H-2-pyranyloxy)-4,10-undecadien-3-ol (1276622-05-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: copper(l) iodide; palladium 10% on activated carbon; potassium carbonate; triphenylphosphine / 1,2-dimethoxyethane; water / 0.5 h / 20 °C / Inert atmosphere

1.2: 5 h / 85 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

2.2: 0 °C

3.1: sodium hydride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

3.2: 6.17 h / 0 - 20 °C / Inert atmosphere

4.1: pyridinium p-toluenesulfonate / methanol / 2 h / 20 °C / Inert atmosphere

5.1: dmap; triethylamine / dichloromethane / 1 h / Inert atmosphere

6.1: potassium carbonate / methanol / 1 h / 20 °C / Inert atmosphere

7.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere

7.2: 2.25 h / -78 °C / Inert atmosphere

8.1: sodium hydride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

8.2: 3.17 h / 0 - 20 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

10.1: lithium aluminium tetrahydride / tetrahydrofuran / 39 h / 0 °C / Inert atmosphere; Reflux

10.2: 0 °C

With dmap; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; water;

DOI:10.1002/cjoc.201190015

Reference yield:

(2S,3E)-1-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-4-phenyl-3-buten-2-ol (1220994-32-0) → (3R,4E,7R,9S,10E)-7,9-di(benzyloxy)-11-phenyl-1-(tetrahydro-2H-2-pyranyloxy)-4,10-undecadien-3-ol (1276622-05-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium hydride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

1.2: 6.17 h / 0 - 20 °C / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / methanol / 2 h / 20 °C / Inert atmosphere

3.1: dmap; triethylamine / dichloromethane / 1 h / Inert atmosphere

4.1: potassium carbonate / methanol / 1 h / 20 °C / Inert atmosphere

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere

5.2: 2.25 h / -78 °C / Inert atmosphere

6.1: sodium hydride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

6.2: 3.17 h / 0 - 20 °C / Inert atmosphere

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

8.1: lithium aluminium tetrahydride / tetrahydrofuran / 39 h / 0 °C / Inert atmosphere; Reflux

8.2: 0 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1002/cjoc.201190015

upstream raw materials:

(S)-(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-but-3-yn-2-ol

(2S,3E)-1-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-4-phenyl-3-buten-2-ol

(2S)-2-[(2S,3E)-2-(benzyloxy)-4-phenylbut-3-en-1-yl]-1,4-dioxaspiro[4.5]decane

(2S)-2-[(2S,3E)-2-(benzyloxy)-4-phenylbut-3-en-1-yl]oxirane

Downstream raw materials:

(3R,4E,7R,9S,10E)-7,9-di(benzyloxy)-3-(methoxymethoxy)-11-phenyl-4,10-undecadien-1-ol

methyl (2Z,5R,6E,9R,11S,12E)-9,11-di(benzyloxy)-5-(methoxymethoxy)-13-phenyl-2,6,12-tridecatrienoate

(6R)-6-[(1E,4R,6S,7E)-4,6-di(benzyloxy)-8-phenyl-1,7-octadienyl]-5,6-dihydro-2H-2-pyranone

2-[(3R,4E,7R,9S,10E)-7,9-di(benzyloxy)-3-(methoxymethoxy)-11-phenyl-4,10-undecadienyl]oxytetrahydro-2H-pyran