(6E,8Z,11Z)-(S)-20-(2-Azido-5-iodo-benzoylamino)-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid

Base Information

• Chemical Name: (6E,8Z,11Z)-(S)-20-(2-Azido-5-iodo-benzoylamino)-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid
• CAS No.: 303039-14-7
• Molecular Formula: C₄₃H₅₅IN₄O₄Si
• Molecular Weight: 846.924
• Mol file: 303039-14-7.mol

Synonyms:(6E,8Z,11Z)-(S)-20-(2-Azido-5-iodo-benzoylamino)-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid

Chemical Property of (6E,8Z,11Z)-(S)-20-(2-Azido-5-iodo-benzoylamino)-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6E,8Z,11Z)-(S)-20-(2-Azido-5-iodo-benzoylamino)-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid

There total 19 articles about (6E,8Z,11Z)-(S)-20-(2-Azido-5-iodo-benzoylamino)-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid 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: 93.0%

(6E,8Z,11Z)-(S)-20-(2-Azido-5-iodo-benzoylamino)-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester (303039-13-6) → (6E,8Z,11Z)-(S)-20-(2-Azido-5-iodo-benzoylamino)-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid (303039-14-7)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 30h;

DOI:10.1016/S0040-4039(00)01064-9

Reference yield:

9-bromononan-1-ol (55362-80-6) → (6E,8Z,11Z)-(S)-20-(2-Azido-5-iodo-benzoylamino)-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid (303039-14-7)

Guidance literature:

Multi-step reaction with 13 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

11: 88 percent / PPh₃ / H₂O; tetrahydrofuran / 14 h / 20 °C

12: 89 percent / EDCI; HOBT; NaHCO₃ / dimethylformamide / 48 h / 0 - 20 °C

13: 93 percent / aq. NaOH / methanol / 30 h / 20 °C

With 1H-imidazole; sodium hydroxide; sodium azide; tetrabutyl ammonium fluoride; iodine; dimethylaluminum chloride; sodium hydrogencarbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; N,N-dimethyl-formamide; 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 / 11: Reduction / 12: Acylation / 13: Hydrolysis;

DOI:10.1016/S0040-4039(00)01064-9

Reference yield:

methyl 5(S)-(tert-butyldiphenylsilyl)oxy-6-oxo-hexanoate (298691-03-9) → (6E,8Z,11Z)-(S)-20-(2-Azido-5-iodo-benzoylamino)-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid (303039-14-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 78 percent / benzene / 4 h / Heating

2: 97 percent / LiHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 20 °C

3: 86 percent / PPTS / ethanol / 3.5 h / 20 °C

4: 82 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

5: 75 percent / LiHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 20 °C

6: 78 percent / PPTS / ethanol / 3.5 h / 20 °C

7: 88 percent / PPh₃; I₂; imidazole / CH₂Cl₂ / 0 - 20 °C

8: 89 percent / NaN₃ / acetone / 16 h / 65 °C

9: 88 percent / PPh₃ / H₂O; tetrahydrofuran / 14 h / 20 °C

10: 89 percent / EDCI; HOBT; NaHCO₃ / dimethylformamide / 48 h / 0 - 20 °C

11: 93 percent / aq. NaOH / methanol / 30 h / 20 °C

With 1H-imidazole; sodium hydroxide; sodium azide; iodine; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene; 1: Wittig olefination / 2: Wittig olefination / 3: Hydrolysis / 4: Oxidation / 5: Wittig olefination / 6: Hydrolysis / 7: Substitution / 8: Substitution / 9: Reduction / 10: Acylation / 11: Hydrolysis;

DOI:10.1016/S0040-4039(00)01064-9

upstream raw materials:

(6E,8Z,11Z)-(S)-20-(2-Azido-5-iodo-benzoylamino)-5-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,11-trienoic acid methyl ester

2-(9-bromononyloxy)tetrahydropyran

9-bromononan-1-ol

<9-((tetrahydro-2H-pyran-2-yl)oxy)nonyl>triphenylphosphonium bromide