(10R,5Z,8Z,11Z,14Z)-10-methyl-eicosa-5,8,11,14-tetraenoic acid N-{2-[(tert-butyldiphenylsilyl) oxy]ethyl}amide

Base Information

Chemical Name:(10R,5Z,8Z,11Z,14Z)-10-methyl-eicosa-5,8,11,14-tetraenoic acid N-{2-[(tert-butyldiphenylsilyl) oxy]ethyl}amide
CAS No.:1384827-02-4
Molecular Formula:C₃₉H₅₇NO₂Si
Molecular Weight:599.973
Hs Code.:

Synonyms:(10R,5Z,8Z,11Z,14Z)-10-methyl-eicosa-5,8,11,14-tetraenoic acid N-{2-[(tert-butyldiphenylsilyl) oxy]ethyl}amide

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Chemical Property of (10R,5Z,8Z,11Z,14Z)-10-methyl-eicosa-5,8,11,14-tetraenoic acid N-{2-[(tert-butyldiphenylsilyl) oxy]ethyl}amide

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Technology Process of (10R,5Z,8Z,11Z,14Z)-10-methyl-eicosa-5,8,11,14-tetraenoic acid N-{2-[(tert-butyldiphenylsilyl) oxy]ethyl}amide

There total 12 articles about (10R,5Z,8Z,11Z,14Z)-10-methyl-eicosa-5,8,11,14-tetraenoic acid N-{2-[(tert-butyldiphenylsilyl) oxy]ethyl}amide 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: 83.0%

: 1384827-01-3
(10R,5Z,8Z,11Z,14Z)-10-methyl-eicosa-5,8,11,14-tetraenoic acid

: 91578-89-1
2-((tert-butyldiphenylsilyl)oxy)ethanamine

: 1384827-02-4
(10R,5Z,8Z,11Z,14Z)-10-methyl-eicosa-5,8,11,14-tetraenoic acid N-{2-[(tert-butyldiphenylsilyl) oxy]ethyl}amide

Guidance literature:: (10R,5Z,8Z,11Z,14Z)-10-methyl-eicosa-5,8,11,14-tetraenoic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

2-((tert-butyldiphenylsilyl)oxy)ethanamine; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1016/j.tet.2012.05.010

Reference yield:

: 1384826-91-8
(Z)-[(8-bromooct-5-en-1-yl)oxy](tert-butyl)diphenylsilane

: 1384827-02-4
(10R,5Z,8Z,11Z,14Z)-10-methyl-eicosa-5,8,11,14-tetraenoic acid N-{2-[(tert-butyldiphenylsilyl) oxy]ethyl}amide

Guidance literature:: Multi-step reaction with 10 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: chromium(VI) oxide; periodic acid / water; acetonitrile / 0 °C

3.1: methanol; diethyl ether / 0.33 h / 0 °C / Inert atmosphere

4.1: acetonitrile / 96 h / 72 - 75 °C / Inert atmosphere

5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 - -60 °C / Inert atmosphere

5.2: 3.25 h / -115 - 20 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.67 h / 0 - 20 °C / Inert atmosphere

6.2: 0 °C / Inert atmosphere

7.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C

8.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

8.2: 1 h / -78 °C / Inert atmosphere

9.1: lithium hydroxide / tetrahydrofuran; water / 24 h / 20 °C / Inert atmosphere

9.2: pH 3

10.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

10.2: 1 h / 20 °C / Inert atmosphere

With chromium(VI) oxide; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; Dess-Martin periodane; periodic acid; 1,1'-carbonyldiimidazole; lithium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile; 5.1: Wittig reaction / 5.2: Wittig reaction / 7.1: Dess-Martin oxidation / 8.1: Wittig reaction / 8.2: Wittig reaction;
DOI:10.1016/j.tet.2012.05.010

Reference yield:

: 928-90-5
5-hexyl-1-ol

: 1384827-02-4
(10R,5Z,8Z,11Z,14Z)-10-methyl-eicosa-5,8,11,14-tetraenoic acid N-{2-[(tert-butyldiphenylsilyl) oxy]ethyl}amide

Guidance literature:: Multi-step reaction with 14 steps

1.1: 1H-imidazole / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

2.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / -78 - 0 °C / Inert atmosphere; Molecular sieve

2.2: 5 h / 0 °C / Inert atmosphere; Molecular sieve

3.1: sodium tetrahydroborate; hydrogen; nickel diacetate; ethylenediamine / methanol / 20 °C / Inert atmosphere

4.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 °C / Inert atmosphere

5.2: Inert atmosphere

6.1: chromium(VI) oxide; periodic acid / water; acetonitrile / 0 °C

7.1: methanol; diethyl ether / 0.33 h / 0 °C / Inert atmosphere

8.1: acetonitrile / 96 h / 72 - 75 °C / Inert atmosphere

9.1: potassium hexamethylsilazane / tetrahydrofuran / 0.75 h / -78 - -60 °C / Inert atmosphere

9.2: 3.25 h / -115 - 20 °C / Inert atmosphere

10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.67 h / 0 - 20 °C / Inert atmosphere

10.2: 0 °C / Inert atmosphere

11.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C

12.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

12.2: 1 h / -78 °C / Inert atmosphere

13.1: lithium hydroxide / tetrahydrofuran; water / 24 h / 20 °C / Inert atmosphere

13.2: pH 3

14.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

14.2: 1 h / 20 °C / Inert atmosphere

With 1H-imidazole; chromium(VI) oxide; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; carbon tetrabromide; tetrabutyl ammonium fluoride; hydrogen; nickel diacetate; potassium hexamethylsilazane; Dess-Martin periodane; periodic acid; ethylenediamine; triphenylphosphine; 1,1'-carbonyldiimidazole; lithium hydroxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetonitrile; 9.1: Wittig reaction / 9.2: Wittig reaction / 11.1: Dess-Martin oxidation / 12.1: Wittig reaction / 12.2: Wittig reaction;
DOI:10.1016/j.tet.2012.05.010