(8E,10E,14Z)-(5S,12R)-5,12-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-8,10,14-trien-6-ynoic acid methyl ester

Base Information

Chemical Name:(8E,10E,14Z)-(5S,12R)-5,12-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-8,10,14-trien-6-ynoic acid methyl ester
CAS No.:90132-08-4
Molecular Formula:C₅₃H₆₈O₄Si₂
Molecular Weight:825.292
Hs Code.:

Synonyms:(8E,10E,14Z)-(5S,12R)-5,12-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-8,10,14-trien-6-ynoic acid methyl ester

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Chemical Property of (8E,10E,14Z)-(5S,12R)-5,12-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-8,10,14-trien-6-ynoic acid methyl ester

Chemical Property:

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Technology Process of (8E,10E,14Z)-(5S,12R)-5,12-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-8,10,14-trien-6-ynoic acid methyl ester

There total 11 articles about (8E,10E,14Z)-(5S,12R)-5,12-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-8,10,14-trien-6-ynoic acid methyl ester 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: 15.0%

: 90108-34-2
(5S,8E,10E,12R)-methyl 5,12-bis<(tert-butyldiphenylsilyl)oxy>-8,10-eicosadiene-6,14-diynoate

: 90108-36-4
(5S,6Z,8E,10E,12R,14Z)-methyl 5,12-bis<(tert-butyldiphenylsilyl)oxy>-6,8,10,14-eicosatetraenoate

: 90132-08-4
(8E,10E,14Z)-(5S,12R)-5,12-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-8,10,14-trien-6-ynoic acid methyl ester

Guidance literature:: With hydrogen; Lindlar's catalyst; In dichloromethane; for 22h; Ambient temperature;
DOI:10.1021/ja00324a024

Reference yield:

: 90108-29-5
(5S)-5-t-butyl diphenyl silyloxy-hept-6-ynoic acid, methyl ester

: 90132-08-4
(8E,10E,14Z)-(5S,12R)-5,12-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-8,10,14-trien-6-ynoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 93 percent / Et₂NH, Pd(PPh₃)4, CuI / 15 h / Ambient temperature

2: 92 percent / PPh₃, CBr₄ / CH₂Cl₂ / -40 - 0 °C

3: 81 percent / aq. AcOH / tetrahydrofuran / 45 °C

4: 75 percent / CrO₃/pyridine / CH₂Cl₂ / 0 °C

5: LDA / tetrahydrofuran / -78 deg C, 8 h; -20 deg C, 1 h; room temp., 1 h

6: 15 percent / H₂ / Lindlar catalyst / CH₂Cl₂ / 22 h / Ambient temperature

With pyridine; chromium(VI) oxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; carbon tetrabromide; hydrogen; acetic acid; diethylamine; triphenylphosphine; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00324a024

Reference yield:

: 90108-31-9
(E)-(S)-10-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-dec-8-en-6-ynoic acid methyl ester

: 90132-08-4
(8E,10E,14Z)-(5S,12R)-5,12-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-8,10,14-trien-6-ynoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 81 percent / aq. AcOH / tetrahydrofuran / 45 °C

2: 75 percent / CrO₃/pyridine / CH₂Cl₂ / 0 °C

3: LDA / tetrahydrofuran / -78 deg C, 8 h; -20 deg C, 1 h; room temp., 1 h

4: 15 percent / H₂ / Lindlar catalyst / CH₂Cl₂ / 22 h / Ambient temperature

With pyridine; chromium(VI) oxide; hydrogen; acetic acid; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00324a024