(E)-3-{(2S,3S)-3-[(6E,8E)-(1S,2S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-acrylic acid

Base Information

• Chemical Name: (E)-3-{(2S,3S)-3-[(6E,8E)-(1S,2S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-acrylic acid
• CAS No.: 85621-22-3
• Molecular Formula: C₃₅H₅₆ClNO₈Si
• Molecular Weight: 682.37
• Mol file: 85621-22-3.mol

Synonyms:

Chemical Property of (E)-3-{(2S,3S)-3-[(6E,8E)-(1S,2S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-acrylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-{(2S,3S)-3-[(6E,8E)-(1S,2S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-acrylic acid

There total 32 articles about (E)-3-{(2S,3S)-3-[(6E,8E)-(1S,2S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-acrylic 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: 85.2%

(E)-3-{(2R,3R)-3-[(6E,8E)-(1R,2R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-acrylic acid methyl ester (91365-95-6) → (E)-3-{(2S,3S)-3-[(6E,8E)-(1S,2S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-acrylic acid (85621-22-3,91422-86-5)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; ethanol; for 17h; Ambient temperature;

DOI:10.1021/jo00193a015

Reference yield:

acrolein dimer (100-73-2) → (E)-3-{(2S,3S)-3-[(6E,8E)-(1S,2S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-acrylic acid (85621-22-3,91422-86-5)

Guidance literature:

Multi-step reaction with 26 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. NaBH₄ 2. 12 N KOH / 1. CH₃OH, 0 deg C, 15 min 2. EtOH-H₂O, reflux, 22 h

23: 1. titanium tetraisopropoxide 2. tert-butyl hydroperoxide / 1. CH₂Cl₂, -20 deg C, 10 min 2. 1,2-dichlorethane, -20 deg C, 1.5 h

24: 440 mg / SO₃*Py, NEt₃ / dimethylsulfoxide / 0.25 h / Ambient temperature

25: 1. sodium hydride / 1. THF, 0 deg C, 10min then 2 h at room temperature 2. THF, 2 h

26: 85.2 percent / 1 N KOH / tetrahydrofuran; ethanol / 17 h / Ambient temperature

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; potassium fluoride; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; pyridine-SO₃ complex; 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; dimethyl sulfoxide; 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 → (E)-3-{(2S,3S)-3-[(6E,8E)-(1S,2S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-acrylic acid (85621-22-3,91422-86-5)

Guidance literature:

Multi-step reaction with 8 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. NaBH₄ 2. 12 N KOH / 1. CH₃OH, 0 deg C, 15 min 2. EtOH-H₂O, reflux, 22 h

5: 1. titanium tetraisopropoxide 2. tert-butyl hydroperoxide / 1. CH₂Cl₂, -20 deg C, 10 min 2. 1,2-dichlorethane, -20 deg C, 1.5 h

6: 440 mg / SO₃*Py, NEt₃ / dimethylsulfoxide / 0.25 h / Ambient temperature

7: 1. sodium hydride / 1. THF, 0 deg C, 10min then 2 h at room temperature 2. THF, 2 h

8: 85.2 percent / 1 N KOH / tetrahydrofuran; ethanol / 17 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; potassium hydroxide; sodium tetrahydroborate; pyridine-SO₃ complex; dipyridine chromium trioxide; sodium hydride; acetic acid; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; pentane;

DOI:10.1021/jo00193a015

upstream raw materials:

(E)-3-{(2R,3R)-3-[(6E,8E)-(1R,2R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-10-(4-chloro-3-methoxy-5-methylamino-phenyl)-4,4,5-trimethoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxiranyl}-acrylic 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