ethyl (4S)-(2Z)-4-<(t-butyldimethylsilyl)oxy>-6-<(4-methoxybenzyloxy)methyl>-7-methyl-3-<(trimethylsilyl)methyl>-2,6-octadienoate

Base Information

• Chemical Name: ethyl (4S)-(2Z)-4-<(t-butyldimethylsilyl)oxy>-6-<(4-methoxybenzyloxy)methyl>-7-methyl-3-<(trimethylsilyl)methyl>-2,6-octadienoate
• CAS No.: 148675-61-0
• Molecular Formula: C₃₀H₅₂O₅Si₂
• Molecular Weight: 548.911
• Mol file: 148675-61-0.mol

Synonyms:ethyl (4S)-(2Z)-4-<(t-butyldimethylsilyl)oxy>-6-<(4-methoxybenzyloxy)methyl>-7-methyl-3-<(trimethylsilyl)methyl>-2,6-octadienoate

Chemical Property of ethyl (4S)-(2Z)-4-<(t-butyldimethylsilyl)oxy>-6-<(4-methoxybenzyloxy)methyl>-7-methyl-3-<(trimethylsilyl)methyl>-2,6-octadienoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (4S)-(2Z)-4-<(t-butyldimethylsilyl)oxy>-6-<(4-methoxybenzyloxy)methyl>-7-methyl-3-<(trimethylsilyl)methyl>-2,6-octadienoate

There total 9 articles about ethyl (4S)-(2Z)-4-<(t-butyldimethylsilyl)oxy>-6-<(4-methoxybenzyloxy)methyl>-7-methyl-3-<(trimethylsilyl)methyl>-2,6-octadienoate 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: 65.0%

(trimethylsilyl)methylmagnesium chloride (13170-43-9) + ethyl (4S)-(2Z)-4-<(t-butyldimethylsilyl)oxy>-3-<(diethylphosphoryl)oxy>-6-<(4-methoxybenzyloxy)methyl>-7-methyl-2,6-octadienoate (148675-60-9) → ethyl (4S)-(2Z)-4-<(t-butyldimethylsilyl)oxy>-6-<(4-methoxybenzyloxy)methyl>-7-methyl-3-<(trimethylsilyl)methyl>-2,6-octadienoate (148675-61-0)

Guidance literature:

bis(acetylacetonate)nickel(II); In diethyl ether; at 0 ℃;

DOI:10.1016/S0040-4020(01)86347-X

Reference yield:

2-isopropylallyl alcohol (26903-66-2) → ethyl (4S)-(2Z)-4-<(t-butyldimethylsilyl)oxy>-6-<(4-methoxybenzyloxy)methyl>-7-methyl-3-<(trimethylsilyl)methyl>-2,6-octadienoate (148675-61-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 1) NaH / 1) THF, DMF, 0 deg C, 30 min, 2) THF, 120 min

2: SnCl₄ / CH₂Cl₂ / 0.08 h / -78 °C

3: 1M aq. NaOH / methanol; tetrahydrofuran / 5 h / Heating

4: DBU / benzene / 5 h / Heating

5: 95 percent / imidazole / dimethylformamide

6: 1) n-BuLi, hexamethyldisilazane, 2) TMEDA / 1) hexane, THF, 0 deg C, 2) -70 deg C, 10 min

7: 1) t-BuOK / 1) THF, 3 min, 2) 15 min

8: 65 percent / Ni(acac)2 / diethyl ether / 0 °C

With 1H-imidazole; sodium hydroxide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate; tin(IV) chloride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1,1,3,3,3-hexamethyl-disilazane; bis(acetylacetonate)nickel(II); In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(01)86347-X

Reference yield:

1-(4-methoxybenzyloxy)-2-(2-propyl)-2-propene (148675-55-2) → ethyl (4S)-(2Z)-4-<(t-butyldimethylsilyl)oxy>-6-<(4-methoxybenzyloxy)methyl>-7-methyl-3-<(trimethylsilyl)methyl>-2,6-octadienoate (148675-61-0)

Guidance literature:

Multi-step reaction with 7 steps

1: SnCl₄ / CH₂Cl₂ / 0.08 h / -78 °C

2: 1M aq. NaOH / methanol; tetrahydrofuran / 5 h / Heating

3: DBU / benzene / 5 h / Heating

4: 95 percent / imidazole / dimethylformamide

5: 1) n-BuLi, hexamethyldisilazane, 2) TMEDA / 1) hexane, THF, 0 deg C, 2) -70 deg C, 10 min

6: 1) t-BuOK / 1) THF, 3 min, 2) 15 min

7: 65 percent / Ni(acac)2 / diethyl ether / 0 °C

With 1H-imidazole; sodium hydroxide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate; tin(IV) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1,1,3,3,3-hexamethyl-disilazane; bis(acetylacetonate)nickel(II); In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(01)86347-X

upstream raw materials:

(trimethylsilyl)methylmagnesium chloride

ethyl (4S)-(2Z)-4-<(t-butyldimethylsilyl)oxy>-3-<(diethylphosphoryl)oxy>-6-<(4-methoxybenzyloxy)methyl>-7-methyl-2,6-octadienoate

2-isopropylallyl alcohol

1-(4-methoxybenzyloxy)-2-(2-propyl)-2-propene