methyl 5-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6(E),8(Z),11(Z),14(Z)-eicosatetraenoate

Base Information

Chemical Name:methyl 5-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6(E),8(Z),11(Z),14(Z)-eicosatetraenoate
CAS No.:108294-19-5
Molecular Formula:C₃₉H₅₆O₃Si
Molecular Weight:600.957
Hs Code.:

Synonyms:methyl 5-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6(E),8(Z),11(Z),14(Z)-eicosatetraenoate

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Chemical Property of methyl 5-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6(E),8(Z),11(Z),14(Z)-eicosatetraenoate

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Technology Process of methyl 5-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6(E),8(Z),11(Z),14(Z)-eicosatetraenoate

There total 9 articles about methyl 5-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6(E),8(Z),11(Z),14(Z)-eicosatetraenoate 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%

: 98582-23-1
diethyl 2(Z),5(Z),8(Z)-tetradecatrienylphosphonate

: methyl 7-<(tert-butyldiphenylsilyl)oxy>-5-formylheptanoate

: 108294-19-5
methyl 5-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6(E),8(Z),11(Z),14(Z)-eicosatetraenoate

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 23 ℃; for 21h;
DOI:10.1021/jm00390a010

Reference yield:

: 98582-21-9
1-<(3,4,5,6-tetrahydro-2-pyranyl)oxy>tetradeca-2,5,8-triyne

: 108294-19-5
methyl 5-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6(E),8(Z),11(Z),14(Z)-eicosatetraenoate

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / H₂ / 10percent Pd/BaSO₄, quinoline / ethyl acetate / 0.75 h / 23 °C / 760 Torr

2: 93 percent / Br₂, 1,2-bis(diphenylphosphino)ethane / CH₂Cl₂ / 9 h / 23 °C

3: 98 percent / acetonitrile / 7 h / 70 - 75 °C

4: 65 percent / lithium diisopropylamide / tetrahydrofuran / 21 h / -78 - 23 °C

With hydrogen; bromine; 1,2-bis-(diphenylphosphino)ethane; lithium diisopropyl amide; quinoline; Pd-BaSO₄; In tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1021/jm00390a010

Reference yield:

: 35378-79-1
undeca-2,5-diyn-1-ol

: 108294-19-5
methyl 5-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-6(E),8(Z),11(Z),14(Z)-eicosatetraenoate

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / Br₂, 1,2-bis(diphenylphosphino)ethane / CH₂Cl₂ / 2 h / 23 °C

2: 1.) EtMgBr, 2.) CuI / 1.) THF, 23 deg C, 10 h, 2.) THF, 23 deg C, 2 h

3: 91 percent / H₂ / 10percent Pd/BaSO₄, quinoline / ethyl acetate / 0.75 h / 23 °C / 760 Torr

4: 93 percent / Br₂, 1,2-bis(diphenylphosphino)ethane / CH₂Cl₂ / 9 h / 23 °C

5: 98 percent / acetonitrile / 7 h / 70 - 75 °C

6: 65 percent / lithium diisopropylamide / tetrahydrofuran / 21 h / -78 - 23 °C

With copper(l) iodide; ethylmagnesium bromide; hydrogen; bromine; 1,2-bis-(diphenylphosphino)ethane; lithium diisopropyl amide; quinoline; Pd-BaSO₄; In tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1021/jm00390a010