(2E,4E,11E,13E)-(6S,7S,10R)-7-(tert-Butyl-dimethyl-silanyloxy)-15-(4-chloro-3-methoxy-5-methylamino-phenyl)-9,9,10-trimethoxy-4,6,14-trimethyl-pentadeca-2,4,11,13-tetraenoic acid

Base Information

• Chemical Name: (2E,4E,11E,13E)-(6S,7S,10R)-7-(tert-Butyl-dimethyl-silanyloxy)-15-(4-chloro-3-methoxy-5-methylamino-phenyl)-9,9,10-trimethoxy-4,6,14-trimethyl-pentadeca-2,4,11,13-tetraenoic acid
• CAS No.: 85621-28-9
• Molecular Formula: C₃₅H₅₆ClNO₇Si
• Molecular Weight: 666.371
• Mol file: 85621-28-9.mol

Synonyms:(2E,4E,11E,13E)-(6S,7S,10R)-7-(tert-Butyl-dimethyl-silanyloxy)-15-(4-chloro-3-methoxy-5-methylamino-phenyl)-9,9,10-trimethoxy-4,6,14-trimethyl-pentadeca-2,4,11,13-tetraenoic acid

Chemical Property of (2E,4E,11E,13E)-(6S,7S,10R)-7-(tert-Butyl-dimethyl-silanyloxy)-15-(4-chloro-3-methoxy-5-methylamino-phenyl)-9,9,10-trimethoxy-4,6,14-trimethyl-pentadeca-2,4,11,13-tetraenoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4E,11E,13E)-(6S,7S,10R)-7-(tert-Butyl-dimethyl-silanyloxy)-15-(4-chloro-3-methoxy-5-methylamino-phenyl)-9,9,10-trimethoxy-4,6,14-trimethyl-pentadeca-2,4,11,13-tetraenoic acid

There total 27 articles about (2E,4E,11E,13E)-(6S,7S,10R)-7-(tert-Butyl-dimethyl-silanyloxy)-15-(4-chloro-3-methoxy-5-methylamino-phenyl)-9,9,10-trimethoxy-4,6,14-trimethyl-pentadeca-2,4,11,13-tetraenoic 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: 66.3%

(2E,4E,11E,13E)-(6S,7S,10R)-7-(tert-Butyl-dimethyl-silanyloxy)-15-[4-chloro-3-methoxy-5-(methoxycarbonyl-methyl-amino)-phenyl]-9,9,10-trimethoxy-4,6,14-trimethyl-pentadeca-2,4,11,13-tetraenoic acid methyl ester (85621-27-8,91422-81-0) → (2E,4E,11E,13E)-(6S,7S,10R)-7-(tert-Butyl-dimethyl-silanyloxy)-15-(4-chloro-3-methoxy-5-methylamino-phenyl)-9,9,10-trimethoxy-4,6,14-trimethyl-pentadeca-2,4,11,13-tetraenoic acid (85621-28-9)

Guidance literature:

With potassium hydroxide; In 1,4-dioxane; methanol; at 90 ℃; for 12h;

DOI:10.1021/jo00193a015

Reference yield: 66.0%

(2E,4E,11E,13E)-(6S,7S,10R)-7-(tert-Butyl-dimethyl-silanyloxy)-15-[4-chloro-3-methoxy-5-(methoxycarbonyl-methyl-amino)-phenyl]-9,9,10-trimethoxy-4,6,14-trimethyl-pentadeca-2,4,11,13-tetraenoic acid methyl ester (85621-27-8,91422-81-0) → (2E,4E,11E,13E)-(6S,7S,10R)-7-(tert-Butyl-dimethyl-silanyloxy)-15-(4-chloro-3-methoxy-5-methylamino-phenyl)-9,9,10-trimethoxy-4,6,14-trimethyl-pentadeca-2,4,11,13-tetraenoic acid (85621-28-9)

Guidance literature:

With potassium hydroxide; In 1,4-dioxane; methanol; at 90 ℃; for 12h;

DOI:10.1246/cl.1982.1907

Reference yield:

acrolein dimer (100-73-2) → (2E,4E,11E,13E)-(6S,7S,10R)-7-(tert-Butyl-dimethyl-silanyloxy)-15-(4-chloro-3-methoxy-5-methylamino-phenyl)-9,9,10-trimethoxy-4,6,14-trimethyl-pentadeca-2,4,11,13-tetraenoic acid (85621-28-9)

Guidance literature:

Multi-step reaction with 23 steps

1: tetrahydrofuran; hexane / Ambient temperature

2: 92 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

4: MCPBA / CH₂Cl₂ / 72 h / Ambient temperature

5: 2. potassium fluoride / 1. -78 deg C/THF/5 min 2. MeOH/1 h/room temperature

6: 1. n-BuLi / 1. THF-HMPA, -78 deg C, 10 min 2. 0 deg C, 30 min

8: 92 percent / methyl orthoformate, d,l-camphersulphonic acid / 18 h / 80 °C

9: 5.6 g / CrO₃*2Py / CH₂Cl₂ / 0.5 h / Ambient temperature

10: 94 percent / d,l-camphersulphonic acid / methanol / 12 h / Ambient temperature

11: 1. NaH / 1. 30 min/THF/0 deg C 2. THF/room temperature/12 h

12: 93 percent / MCPBA / CH₂Cl₂ / 0.5 h / 0 °C

13: 70 percent / NaBH₄ / ethanol; tetrahydrofuran / 1 h / 80 °C

14: 95 percent / pyridine / CH₂Cl₂ / 0.17 h / 0 °C

15: 95 percent / imidazole / dimethylformamide / 30 h / 70 °C

16: 1. ozone 2. NEt₃ / 1. -78 deg C/CH₂Cl₂ 2. 20 h/room temperature

17: 1.66 g / pyridinium tosylate / methanol / 48 h / 0 °C

18: 1.67 g / NaOCH₃ / methanol / 0.75 h / Ambient temperature

19: 1.45 g / CrO₃*2Py / CH₂Cl₂ / 0.25 h / Ambient temperature

20: 78 percent / tetrahydrofuran; dimethylformamide; pentane / 17 h

21: 1.46 g / acetic acid / tetrahydrofuran; H₂O / 48 h / -10 °C

22: 1. n-butyllithium / 1. THF/room temperature/2 h 2. addition at -78 deg C, then 4.5 h/room temperature

23: 66.3 percent / 12 N KOH / methanol; dioxane / 12 h / 90 °C

With pyridine; 1H-imidazole; potassium fluoride; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; 10-camphorsufonic acid; sodium methylate; pyridinium p-toluenesulfonate; dipyridine chromium trioxide; sodium hydride; ozone; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; trimethyl orthoformate; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; pentane;

DOI:10.1021/jo00193a015

upstream raw materials:

(2E,4E,11E,13E)-(6S,7S,10R)-7-(tert-Butyl-dimethyl-silanyloxy)-15-[4-chloro-3-methoxy-5-(methoxycarbonyl-methyl-amino)-phenyl]-9,9,10-trimethoxy-4,6,14-trimethyl-pentadeca-2,4,11,13-tetraenoic acid methyl ester

acrolein dimer

(1S,2S,4S,6S)-4-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-2-(2-methoxy-ethoxy)-3,7-dioxa-bicyclo[4.1.0]heptane

(E)-(2S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-2,3,3,9,9-pentamethoxy-6,8-dimethyl-non-7-enal