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

Base Information

• Chemical Name: methyl (2Z,5R,6E,9R,11S,12E)-9,11-di(benzyloxy)-5-(methoxymethoxy)-13-phenyl-2,6,12-tridecatrienoate
• CAS No.: 1276622-10-6
• Molecular Formula: C₃₆H₄₂O₆
• Molecular Weight: 570.726
• Mol file: 1276622-10-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about methyl (2Z,5R,6E,9R,11S,12E)-9,11-di(benzyloxy)-5-(methoxymethoxy)-13-phenyl-2,6,12-tridecatrienoate 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:

C33H38O5 + bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (88738-78-7) → methyl (2Z,5R,6E,9R,11S,12E)-9,11-di(benzyloxy)-5-(methoxymethoxy)-13-phenyl-2,6,12-tridecatrienoate (1276622-10-6)

Guidance literature:

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

C₃₃H₃₈O₅; In tetrahydrofuran; at -78 ℃; for 0.666667h; Inert atmosphere;

With ammonium chloride; In tetrahydrofuran; water; diastereoselective reaction;

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) → methyl (2Z,5R,6E,9R,11S,12E)-9,11-di(benzyloxy)-5-(methoxymethoxy)-13-phenyl-2,6,12-tridecatrienoate (1276622-10-6)

Guidance literature:

Multi-step reaction with 14 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

11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

12.1: pyridinium p-toluenesulfonate / methanol / 4 h / 20 °C / Inert atmosphere

13.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 3 h / 20 °C / Inert atmosphere

14.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

14.2: 0.67 h / -78 °C / Inert atmosphere

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; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; water; dimethyl sulfoxide; 14.2: Still-Gennari reaction;

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) → methyl (2Z,5R,6E,9R,11S,12E)-9,11-di(benzyloxy)-5-(methoxymethoxy)-13-phenyl-2,6,12-tridecatrienoate (1276622-10-6)

Guidance literature:

Multi-step reaction with 12 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

9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

10.1: pyridinium p-toluenesulfonate / methanol / 4 h / 20 °C / Inert atmosphere

11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 3 h / 20 °C / Inert atmosphere

12.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

12.2: 0.67 h / -78 °C / Inert atmosphere

With dmap; lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; 12.2: Still-Gennari reaction;

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:

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