(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

Base Information

Chemical Name:(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
CAS No.:85621-27-8
Molecular Formula:C₃₈H₆₀ClNO₉Si
Molecular Weight:738.434
Hs Code.:

(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

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Chemical Property of (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

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Technology Process of (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

There total 26 articles about (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 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:

: 100-73-2
acrolein dimer

: 85621-27-8,91422-81-0
(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

Guidance literature:: Multi-step reaction with 22 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

With pyridine; 1H-imidazole; potassium fluoride; 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; methanol; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; pentane;
DOI:10.1021/jo00193a015

Reference yield:

: (E)-(2S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-2,3,3,9,9-pentamethoxy-6,8-dimethyl-non-7-en-1-ol

: 85621-27-8,91422-81-0
(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

Guidance literature:: Multi-step reaction with 4 steps

1: 1.45 g / CrO₃*2Py / CH₂Cl₂ / 0.25 h / Ambient temperature

2: 78 percent / tetrahydrofuran; dimethylformamide; pentane / 17 h

3: 1.46 g / acetic acid / tetrahydrofuran; H₂O / 48 h / -10 °C

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

With n-butyllithium; dipyridine chromium trioxide; acetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; pentane;
DOI:10.1021/jo00193a015

Reference yield:

: 77890-94-9
(1S,2S,4S,6S)-4-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-2-(2-methoxy-ethoxy)-3,7-dioxa-bicyclo[4.1.0]heptane

: 85621-27-8,91422-81-0
(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

Guidance literature:: Multi-step reaction with 17 steps

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

3: 92 percent / methyl orthoformate, d,l-camphersulphonic acid / 18 h / 80 °C

4: 5.6 g / CrO₃*2Py / CH₂Cl₂ / 0.5 h / Ambient temperature

5: 94 percent / d,l-camphersulphonic acid / methanol / 12 h / Ambient temperature

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

7: 93 percent / MCPBA / CH₂Cl₂ / 0.5 h / 0 °C

8: 70 percent / NaBH₄ / ethanol; tetrahydrofuran / 1 h / 80 °C

9: 95 percent / pyridine / CH₂Cl₂ / 0.17 h / 0 °C

10: 95 percent / imidazole / dimethylformamide / 30 h / 70 °C

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

12: 1.66 g / pyridinium tosylate / methanol / 48 h / 0 °C

13: 1.67 g / NaOCH₃ / methanol / 0.75 h / Ambient temperature

14: 1.45 g / CrO₃*2Py / CH₂Cl₂ / 0.25 h / Ambient temperature

15: 78 percent / tetrahydrofuran; dimethylformamide; pentane / 17 h

16: 1.46 g / acetic acid / tetrahydrofuran; H₂O / 48 h / -10 °C

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

With pyridine; 1H-imidazole; 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; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; pentane;
DOI:10.1021/jo00193a015