(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

Base Information

Chemical Name:(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
CAS No.:91365-95-6
Molecular Formula:C₃₆H₅₈ClNO₈Si
Molecular Weight:696.397
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 29 articles about (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 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

: 91365-95-6
(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

Guidance literature:: Multi-step reaction with 25 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

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

: 91365-95-6
(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

Guidance literature:: Multi-step reaction with 7 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

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

: 91365-95-6
(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

Guidance literature:: Multi-step reaction with 20 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. NaBH₄ 2. 12 N KOH / 1. CH₃OH, 0 deg C, 15 min 2. EtOH-H₂O, reflux, 22 h

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

19: 440 mg / SO₃*Py, NEt₃ / dimethylsulfoxide / 0.25 h / Ambient temperature

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

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; 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; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; pentane;
DOI:10.1021/jo00193a015