(2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-7-(tert-Butyl-dimethyl-silanyloxy)-15-[2,5-dimethoxy-3-(2,2,2-trifluoro-acetylamino)-phenyl]-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid ethyl ester

Base Information

• Chemical Name: (2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-7-(tert-Butyl-dimethyl-silanyloxy)-15-[2,5-dimethoxy-3-(2,2,2-trifluoro-acetylamino)-phenyl]-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid ethyl ester
• CAS No.: 123083-97-6
• Molecular Formula: C₄₁H₆₆F₃NO₉Si
• Molecular Weight: 802.057
• Mol file: 123083-97-6.mol

Synonyms:

Chemical Property of (2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-7-(tert-Butyl-dimethyl-silanyloxy)-15-[2,5-dimethoxy-3-(2,2,2-trifluoro-acetylamino)-phenyl]-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-7-(tert-Butyl-dimethyl-silanyloxy)-15-[2,5-dimethoxy-3-(2,2,2-trifluoro-acetylamino)-phenyl]-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid ethyl ester

There total 23 articles about (2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-7-(tert-Butyl-dimethyl-silanyloxy)-15-[2,5-dimethoxy-3-(2,2,2-trifluoro-acetylamino)-phenyl]-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid ethyl 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:

t-butyldimethylsiyl triflate (69739-34-0) → (2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-7-(tert-Butyl-dimethyl-silanyloxy)-15-[2,5-dimethoxy-3-(2,2,2-trifluoro-acetylamino)-phenyl]-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid ethyl ester (123083-97-6)

Guidance literature:

Multi-step reaction with 13 steps

1: 100 percent / 2,6-Lutidine / CH₂Cl₂ / 1.5 h / -5 °C

2: 98 percent / DIBAL-H / toluene / -20 deg C, 1 h

3: 100 percent / Imidazole / dimethylformamide / 20 h / Ambient temperature

5: 96 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) room temperature, 6 h

6: 96 percent / HF*Py-Py-THF / methanol / 6.5 h / Ambient temperature

7: 89 percent / SO₃*Py, DMSO, NEt₃ / tetrahydrofuran / 0.25 h / Ambient temperature

8: 1.) KN(SiMe₃)2 / 1.) 18-crown-6 / 1.) toluene, THF, 10 min, -80 degC, 2.) THF, 1 h, -78 deg C

9: 99 percent / DIBAL-H / toluene / 1 h / -33 °C

10: 70 percent / Hydroxylamine Hydrochloride, KOH / ethanol; H₂O / 48 h / Heating

11: 95 percent / NEt₃ / CH₂Cl₂ / 0.67 h / Ambient temperature

12: 95 percent / Pyridinium dichromate / CH₂Cl₂ / 6.5 h / Ambient temperature

13: CH₂Cl₂ / 40 h / Heating

With tetrahydrofuran; pyridine; 1H-imidazole; 2,6-dimethylpyridine; potassium hydroxide; dipyridinium dichromate; pyridine-SO₃ complex; hydroxylamine hydrochloride; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; 18-crown-6 ether; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1039/P19900000047

Reference yield:

(4R,5S)-3-((E)-(2R,3R)-3-Hydroxy-5-iodo-2,4-dimethyl-pent-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one (106484-90-6) → (2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-7-(tert-Butyl-dimethyl-silanyloxy)-15-[2,5-dimethoxy-3-(2,2,2-trifluoro-acetylamino)-phenyl]-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid ethyl ester (123083-97-6)

Guidance literature:

Multi-step reaction with 15 steps

1: 98 percent / 2,6-Lutidine / CH₂Cl₂ / 2 h / 0 °C

2: 84 percent / 30percent H₂O₂, aq. LiOH / tetrahydrofuran; H₂O / 2 h / 5 °C

3: 99 percent / NaH / dimethylformamide; tetrahydrofuran / 1.) -10 deg C, 0,5 h 2.) 2,5 h, room temperature

4: 98 percent / DIBAL-H / toluene / -20 deg C, 1 h

5: 100 percent / Imidazole / dimethylformamide / 20 h / Ambient temperature

7: 96 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) room temperature, 6 h

8: 96 percent / HF*Py-Py-THF / methanol / 6.5 h / Ambient temperature

9: 89 percent / SO₃*Py, DMSO, NEt₃ / tetrahydrofuran / 0.25 h / Ambient temperature

10: 1.) KN(SiMe₃)2 / 1.) 18-crown-6 / 1.) toluene, THF, 10 min, -80 degC, 2.) THF, 1 h, -78 deg C

11: 99 percent / DIBAL-H / toluene / 1 h / -33 °C

12: 70 percent / Hydroxylamine Hydrochloride, KOH / ethanol; H₂O / 48 h / Heating

13: 95 percent / NEt₃ / CH₂Cl₂ / 0.67 h / Ambient temperature

14: 95 percent / Pyridinium dichromate / CH₂Cl₂ / 6.5 h / Ambient temperature

15: CH₂Cl₂ / 40 h / Heating

With tetrahydrofuran; pyridine; 1H-imidazole; 2,6-dimethylpyridine; potassium hydroxide; lithium hydroxide; dipyridinium dichromate; pyridine-SO₃ complex; hydroxylamine hydrochloride; dihydrogen peroxide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; 18-crown-6 ether; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1039/P19900000047

Reference yield:

(E)-(2S,3S)-3-Hydroxy-5-iodo-2,4-dimethyl-pent-4-enoic acid methyl ester (123084-04-8) → (2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-7-(tert-Butyl-dimethyl-silanyloxy)-15-[2,5-dimethoxy-3-(2,2,2-trifluoro-acetylamino)-phenyl]-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid ethyl ester (123083-97-6)

Guidance literature:

Multi-step reaction with 13 steps

1: 100 percent / 2,6-Lutidine / CH₂Cl₂ / 1.5 h / -5 °C

2: 98 percent / DIBAL-H / toluene / -20 deg C, 1 h

3: 100 percent / Imidazole / dimethylformamide / 20 h / Ambient temperature

5: 96 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) room temperature, 6 h

6: 96 percent / HF*Py-Py-THF / methanol / 6.5 h / Ambient temperature

7: 89 percent / SO₃*Py, DMSO, NEt₃ / tetrahydrofuran / 0.25 h / Ambient temperature

8: 1.) KN(SiMe₃)2 / 1.) 18-crown-6 / 1.) toluene, THF, 10 min, -80 degC, 2.) THF, 1 h, -78 deg C

9: 99 percent / DIBAL-H / toluene / 1 h / -33 °C

10: 70 percent / Hydroxylamine Hydrochloride, KOH / ethanol; H₂O / 48 h / Heating

11: 95 percent / NEt₃ / CH₂Cl₂ / 0.67 h / Ambient temperature

12: 95 percent / Pyridinium dichromate / CH₂Cl₂ / 6.5 h / Ambient temperature

13: CH₂Cl₂ / 40 h / Heating

With tetrahydrofuran; pyridine; 1H-imidazole; 2,6-dimethylpyridine; potassium hydroxide; dipyridinium dichromate; pyridine-SO₃ complex; hydroxylamine hydrochloride; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; 18-crown-6 ether; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1039/P19900000047

upstream raw materials:

N-{3-[(7E,11Z)-(1R,2S,4S,5R,6S,9R,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-1,4,5-trimethoxy-2,6,8,10-tetramethyl-13-oxo-trideca-7,11-dienyl]-2,5-dimethoxy-phenyl}-2,2,2-trifluoro-acetamide

ethyl (triphenylphosphoranylidene)acetate

t-butyldimethylsiyl triflate

(E)-(2S,3S)-3-Hydroxy-5-iodo-2,4-dimethyl-pent-4-enoic acid methyl ester

Downstream raw materials:

macbecin I