(11E,16E)-(2R,5S,7R,10S,15S)-10-Ethyl-7,11,15,17-tetramethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-dione

Base Information

• Chemical Name: (11E,16E)-(2R,5S,7R,10S,15S)-10-Ethyl-7,11,15,17-tetramethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-dione
• CAS No.: 180062-76-4
• Molecular Formula: C₃₁H₄₂O₅
• Molecular Weight: 494.671
• Mol file: 180062-76-4.mol

Synonyms:(11E,16E)-(2R,5S,7R,10S,15S)-10-Ethyl-7,11,15,17-tetramethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-dione

Chemical Property of (11E,16E)-(2R,5S,7R,10S,15S)-10-Ethyl-7,11,15,17-tetramethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (11E,16E)-(2R,5S,7R,10S,15S)-10-Ethyl-7,11,15,17-tetramethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-dione

There total 16 articles about (11E,16E)-(2R,5S,7R,10S,15S)-10-Ethyl-7,11,15,17-tetramethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-dione 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:

5-(tert-butyldimethylsilanyloxy)-4(S)-methylpentan-2-one (179944-08-2) → (11E,16E)-(2R,5S,7R,10S,15S)-10-Ethyl-7,11,15,17-tetramethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-dione (180062-76-4)

Guidance literature:

Multi-step reaction with 13 steps

1: 1.) t-BuLi / 1.) ether, pentane, -78 deg C, 90 min, 2.) ether, THF, pentane, -78 deg C, 2 h

2: 1.) Martin's sulfurane reagent, 2.) Et₄NF / 1.) CH₂Cl₂, RT, 2.) DMF, RT, overnight

3: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 15 min

4: 1.) LiCl, DBU / 1.) CH₃CN, RT, 2.) CH₃CN, 0 deg C, 1 h

5: 96 percent / DIBAL-H / CH₂Cl₂; hexane / 2 h / -78 °C

6: I₂, PPh₃, imidazole / diethyl ether; acetonitrile / 0.5 h / -30 °C

7: LiHMDS, HMPA / tetrahydrofuran / 1 h / -78 °C

8: Et₄NF, 4 Angstroem molecular sieves / dimethylsulfoxide / 90 °C

9: diethyl ether / 0.08 h / Ambient temperature

10: 99 percent / pyridine, DMAP / 1 h / Ambient temperature

11: 75 percent / LiHMDS / tetrahydrofuran / 1 h / Heating

12: 1.) KOt-Bu / 1.) DMF, THF, 0 deg C, 10 min, 2.) DMF, THF, 0 deg C, 1 h

13: 1.) KOt-Bu, 2.) gl. AcOH / 1.) DMF, THF, 0 deg C, 10 min

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; oxalyl dichloride; Martins sulfurane; 4 A molecular sieve; potassium tert-butylate; iodine; tert.-butyl lithium; diisobutylaluminium hydride; tetraethylammonium fluoride; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile;

DOI:10.1021/ja961344l

Reference yield:

(S)-3-(2-trimethylsilylethoxymethoxy)pentan-2-one (179944-05-9) → (11E,16E)-(2R,5S,7R,10S,15S)-10-Ethyl-7,11,15,17-tetramethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-dione (180062-76-4)

Guidance literature:

Multi-step reaction with 14 steps

1: CrCl₂ / tetrahydrofuran / 0 °C

2: 1.) t-BuLi / 1.) ether, pentane, -78 deg C, 90 min, 2.) ether, THF, pentane, -78 deg C, 2 h

3: 1.) Martin's sulfurane reagent, 2.) Et₄NF / 1.) CH₂Cl₂, RT, 2.) DMF, RT, overnight

4: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 15 min

5: 1.) LiCl, DBU / 1.) CH₃CN, RT, 2.) CH₃CN, 0 deg C, 1 h

6: 96 percent / DIBAL-H / CH₂Cl₂; hexane / 2 h / -78 °C

7: I₂, PPh₃, imidazole / diethyl ether; acetonitrile / 0.5 h / -30 °C

8: LiHMDS, HMPA / tetrahydrofuran / 1 h / -78 °C

9: Et₄NF, 4 Angstroem molecular sieves / dimethylsulfoxide / 90 °C

10: diethyl ether / 0.08 h / Ambient temperature

11: 99 percent / pyridine, DMAP / 1 h / Ambient temperature

12: 75 percent / LiHMDS / tetrahydrofuran / 1 h / Heating

13: 1.) KOt-Bu / 1.) DMF, THF, 0 deg C, 10 min, 2.) DMF, THF, 0 deg C, 1 h

14: 1.) KOt-Bu, 2.) gl. AcOH / 1.) DMF, THF, 0 deg C, 10 min

With pyridine; 1H-imidazole; chromium dichloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; oxalyl dichloride; Martins sulfurane; 4 A molecular sieve; potassium tert-butylate; iodine; tert.-butyl lithium; diisobutylaluminium hydride; tetraethylammonium fluoride; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile;

DOI:10.1021/ja961344l

Reference yield:

(E)-(2S,7S)-2,6-Dimethyl-4-methylene-7-(2-trimethylsilanyl-ethoxymethoxy)-non-5-en-1-ol (179944-18-4) → (11E,16E)-(2R,5S,7R,10S,15S)-10-Ethyl-7,11,15,17-tetramethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-dione (180062-76-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 15 min

2: 1.) LiCl, DBU / 1.) CH₃CN, RT, 2.) CH₃CN, 0 deg C, 1 h

3: 96 percent / DIBAL-H / CH₂Cl₂; hexane / 2 h / -78 °C

4: I₂, PPh₃, imidazole / diethyl ether; acetonitrile / 0.5 h / -30 °C

5: LiHMDS, HMPA / tetrahydrofuran / 1 h / -78 °C

6: Et₄NF, 4 Angstroem molecular sieves / dimethylsulfoxide / 90 °C

7: diethyl ether / 0.08 h / Ambient temperature

8: 99 percent / pyridine, DMAP / 1 h / Ambient temperature

9: 75 percent / LiHMDS / tetrahydrofuran / 1 h / Heating

10: 1.) KOt-Bu / 1.) DMF, THF, 0 deg C, 10 min, 2.) DMF, THF, 0 deg C, 1 h

11: 1.) KOt-Bu, 2.) gl. AcOH / 1.) DMF, THF, 0 deg C, 10 min

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; oxalyl dichloride; 4 A molecular sieve; potassium tert-butylate; iodine; diisobutylaluminium hydride; tetraethylammonium fluoride; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile;

DOI:10.1021/ja961344l

upstream raw materials:

(11E,16E)-(2R,5S,7S,10S,15S)-10-Ethyl-7,11,15,17-tetramethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-dione

5-(tert-butyldimethylsilanyloxy)-4(S)-methylpentan-2-one

(S)-3-(2-trimethylsilylethoxymethoxy)pentan-2-one

(E)-(2S,7S)-2,6-Dimethyl-4-methylene-7-(2-trimethylsilanyl-ethoxymethoxy)-non-5-en-1-ol

Downstream raw materials:

galbonolide B

Refernces