4-[1-hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enyl]-11-methyl-8-triethylsilanyloxy-9-vinyl-2,6-dioxa-tricyclo[5.2.2.0^1,5]undec-4-en-3-one

Base Information

• Chemical Name: 4-[1-hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enyl]-11-methyl-8-triethylsilanyloxy-9-vinyl-2,6-dioxa-tricyclo[5.2.2.0^1,5]undec-4-en-3-one
• CAS No.: 926290-19-9
• Molecular Formula: C₃₅H₅₂O₇Si
• Molecular Weight: 612.879
• Mol file: 926290-19-9.mol

Synonyms:4-[1-hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enyl]-11-methyl-8-triethylsilanyloxy-9-vinyl-2,6-dioxa-tricyclo[5.2.2.0^1,5]undec-4-en-3-one

Chemical Property of 4-[1-hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enyl]-11-methyl-8-triethylsilanyloxy-9-vinyl-2,6-dioxa-tricyclo[5.2.2.0^1,5]undec-4-en-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[1-hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enyl]-11-methyl-8-triethylsilanyloxy-9-vinyl-2,6-dioxa-tricyclo[5.2.2.0^1,5]undec-4-en-3-one

There total 16 articles about 4-[1-hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enyl]-11-methyl-8-triethylsilanyloxy-9-vinyl-2,6-dioxa-tricyclo[5.2.2.0^1,5]undec-4-en-3-one 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-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enal (926289-97-6) + 11-methyl-8-triethylsilanyloxy-9-vinyl-2,6-dioxa-tricyclo[5.2.2.01,5]undec-4-en-3-one (903504-33-6) → 4-[1-hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enyl]-11-methyl-8-triethylsilanyloxy-9-vinyl-2,6-dioxa-tricyclo[5.2.2.01,5]undec-4-en-3-one (926290-19-9)

Guidance literature:

11-methyl-8-triethylsilanyloxy-9-vinyl-2,6-dioxa-tricyclo[5.2.2.0^1,5]undec-4-en-3-one; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 0.5h;

5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enal; In tetrahydrofuran; pentane; for 0.166667h;

DOI:10.1021/ja067083p

Reference yield:

(2R,3E,5E)-1-(phenylthio)hepta-3,5-dien-2-ol (903504-28-9) → 4-[1-hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enyl]-11-methyl-8-triethylsilanyloxy-9-vinyl-2,6-dioxa-tricyclo[5.2.2.01,5]undec-4-en-3-one (926290-19-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 2-(pyrrolidin-1-yl)phenol; MeMgBr / toluene; diethyl ether / 1.5 h / 4 °C

1.2: toluene; diethyl ether / 18 h / 55 °C

2.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: O₂ (gas); (EtO)3P / tetrahydrofuran

3.1: lithium 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / 3 h / -48 °C

4.1: K₂CO₃ / dimethylformamide / 0.17 h / 60 °C

5.1: t-BuOOH; VO(OEt)3 / CH₂Cl₂; toluene / 4 h

6.1: Et₃N; 4-DMAP / 12 h / 20 °C

7.1: LiHMDS / 1.17 h / -78 - 25 °C

7.2: tetrahydrofuran / 2 h / Heating

8.1: 4-DMAP; imidazole / dimethylformamide / 2 h / 20 °C

9.1: t-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C

9.2: 92 mg / tetrahydrofuran; pentane / 0.17 h

With 1H-imidazole; tert.-butylhydroperoxide; dmap; 2-(pyrrolidin-1-yl)phenol; methylmagnesium bromide; tert.-butyl lithium; vanadium(V) oxytriethoxide; lithium 4,4′-di-tert-butylbiphenylide; potassium carbonate; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; pentane; 1.2: Diels-Alder reaction;

DOI:10.1021/ja067083p

Reference yield:

1-hydroxy-5-methyl-2-vinyl-cyclohex-3-enecarboxylic acid → 4-[1-hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enyl]-11-methyl-8-triethylsilanyloxy-9-vinyl-2,6-dioxa-tricyclo[5.2.2.01,5]undec-4-en-3-one (926290-19-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: K₂CO₃ / dimethylformamide / 0.17 h / 60 °C

2.1: t-BuOOH; VO(OEt)3 / CH₂Cl₂; toluene / 4 h

3.1: Et₃N; 4-DMAP / 12 h / 20 °C

4.1: LiHMDS / 1.17 h / -78 - 25 °C

4.2: tetrahydrofuran / 2 h / Heating

5.1: 4-DMAP; imidazole / dimethylformamide / 2 h / 20 °C

6.1: t-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C

6.2: 92 mg / tetrahydrofuran; pentane / 0.17 h

With 1H-imidazole; tert.-butylhydroperoxide; dmap; tert.-butyl lithium; vanadium(V) oxytriethoxide; potassium carbonate; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; pentane;

DOI:10.1021/ja067083p

upstream raw materials:

5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enal

11-methyl-8-triethylsilanyloxy-9-vinyl-2,6-dioxa-tricyclo[5.2.2.0^1,5]undec-4-en-3-one

(3E,5E)-1-(phenylthio)hepta-3,5-dien-2-one

(2R,3E,5E)-1-(phenylthio)hepta-3,5-dien-2-ol