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

Base Information

• Chemical Name: (6R)-6-[(1E,4R,6S,7E)-4,6-di(benzyloxy)-8-phenyl-1,7-octadienyl]-5,6-dihydro-2H-2-pyranone
• CAS No.: 1276621-90-9
• Molecular Formula: C₃₃H₃₄O₄
• Molecular Weight: 494.631
• Mol file: 1276621-90-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about (6R)-6-[(1E,4R,6S,7E)-4,6-di(benzyloxy)-8-phenyl-1,7-octadienyl]-5,6-dihydro-2H-2-pyranone 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: 76.0%

methyl (2Z,5R,6E,9R,11S,12E)-9,11-di(benzyloxy)-5-(methoxymethoxy)-13-phenyl-2,6,12-tridecatrienoate (1276622-10-6) → (6R)-6-[(1E,4R,6S,7E)-4,6-di(benzyloxy)-8-phenyl-1,7-octadienyl]-5,6-dihydro-2H-2-pyranone (1276621-90-9)

Guidance literature:

With cerium(III) chloride heptahydrate; In methanol; acetonitrile; for 4h; Inert atmosphere; Reflux;

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) → (6R)-6-[(1E,4R,6S,7E)-4,6-di(benzyloxy)-8-phenyl-1,7-octadienyl]-5,6-dihydro-2H-2-pyranone (1276621-90-9)

Guidance literature:

Multi-step reaction with 13 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

13.1: cerium(III) chloride heptahydrate / methanol; acetonitrile / 4 h / Inert atmosphere; Reflux

With dmap; lithium aluminium tetrahydride; n-butyllithium; cerium(III) chloride heptahydrate; 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; acetonitrile; 12.2: Still-Gennari 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) → (6R)-6-[(1E,4R,6S,7E)-4,6-di(benzyloxy)-8-phenyl-1,7-octadienyl]-5,6-dihydro-2H-2-pyranone (1276621-90-9)

Guidance literature:

Multi-step reaction with 15 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

15.1: cerium(III) chloride heptahydrate / methanol; acetonitrile / 4 h / Inert atmosphere; Reflux

With dmap; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; cerium(III) chloride heptahydrate; 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; acetonitrile; 14.2: 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