(6E,8Z,11Z)-(S)-20-Azido-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester

Base Information

Chemical Name:(6E,8Z,11Z)-(S)-20-Azido-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester
CAS No.:298691-10-8
Molecular Formula:C₃₇H₅₃N₃O₃Si
Molecular Weight:615.932
Hs Code.:

Synonyms:(6E,8Z,11Z)-(S)-20-Azido-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester

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Chemical Property of (6E,8Z,11Z)-(S)-20-Azido-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester

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Technology Process of (6E,8Z,11Z)-(S)-20-Azido-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester

There total 26 articles about (6E,8Z,11Z)-(S)-20-Azido-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic 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: 89.0%

: 303039-12-5
(6E,8Z,11Z)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-20-iodo-icosa-6,8,11-trienoic acid methyl ester

: 298691-10-8
(6E,8Z,11Z)-(S)-20-Azido-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester

Guidance literature:: With sodium azide; In acetone; at 65 ℃; for 16h;
DOI:10.1016/S0040-4039(00)01064-9

Reference yield: 36.0%

: 298691-04-0
9-azidononanal

: [(3Z,5E)-(S)-7-(tert-Butyl-diphenyl-silanyloxy)-10-methoxycarbonyl-deca-3,5-dienyl]-triphenyl-phosphonium; iodide

: 298691-10-8
(6E,8Z,11Z)-(S)-20-Azido-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester

Guidance literature:: With lithium hexamethyldisilazane; at -78 - 20 ℃;
DOI:10.1016/S0040-4039(00)00971-0

Reference yield:

: 55362-80-6
9-bromononan-1-ol

: 298691-10-8
(6E,8Z,11Z)-(S)-20-Azido-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 89 percent / PTSA / 2 h / 0 - 20 °C

2: 94 percent / acetonitrile / 38 h / 70 °C

3: 78 percent / LiHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 20 °C

4: 94 percent / TBAF / 28 h / 20 °C

5: 92 percent / PPh₃; I₂; imidazole / CH₂Cl₂ / 2 h / 0 - 20 °C

6: 95 percent / acetonitrile / 48 h / 70 °C

7: 85 percent / LiHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 20 °C

8: 75 percent / Me₂AlCl / CH₂Cl₂ / 1.5 h / -30 - 20 °C

9: 88 percent / PPh₃; I₂; imidazole / CH₂Cl₂ / 0 - 20 °C

10: 89 percent / NaN₃ / acetone / 16 h / 65 °C

With 1H-imidazole; sodium azide; tetrabutyl ammonium fluoride; iodine; dimethylaluminum chloride; toluene-4-sulfonic acid; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; acetone; acetonitrile; 1: acetalisation / 2: Substitution / 3: Wittig olefination / 4: Hydrolysis / 5: Substitution / 6: Substitution / 7: Wittig olefination / 8: acetal cleavage / 9: Substitution / 10: Substitution;
DOI:10.1016/S0040-4039(00)01064-9