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

Base Information

• Chemical Name: N-{3-[(7E,11Z)-(1R,2S,4S,5R,6S,9R,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-13-hydroxy-1,4,5-trimethoxy-2,6,8,10-tetramethyl-trideca-7,11-dienyl]-2,5-dimethoxy-phenyl}-2,2,2-trifluoro-acetamide
• CAS No.: 123083-96-5
• Molecular Formula: C₃₆H₆₀F₃NO₈Si
• Molecular Weight: 719.955
• Mol file: 123083-96-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 21 articles about N-{3-[(7E,11Z)-(1R,2S,4S,5R,6S,9R,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-13-hydroxy-1,4,5-trimethoxy-2,6,8,10-tetramethyl-trideca-7,11-dienyl]-2,5-dimethoxy-phenyl}-2,2,2-trifluoro-acetamide 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: 95.0%

(2Z,6E)-(4S,5R,8S,9R,10S,12S,13R)-13-(3-Amino-2,5-dimethoxy-phenyl)-5-(tert-butyl-dimethyl-silanyloxy)-9,10,13-trimethoxy-4,6,8,12-tetramethyl-trideca-2,6-dien-1-ol (123083-95-4) + trifluoroacetic anhydride (407-25-0) → N-{3-[(7E,11Z)-(1R,2S,4S,5R,6S,9R,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-13-hydroxy-1,4,5-trimethoxy-2,6,8,10-tetramethyl-trideca-7,11-dienyl]-2,5-dimethoxy-phenyl}-2,2,2-trifluoro-acetamide (123083-96-5)

Guidance literature:

With triethylamine; In dichloromethane; for 0.666667h; Ambient temperature;

DOI:10.1039/P19900000047

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → N-{3-[(7E,11Z)-(1R,2S,4S,5R,6S,9R,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-13-hydroxy-1,4,5-trimethoxy-2,6,8,10-tetramethyl-trideca-7,11-dienyl]-2,5-dimethoxy-phenyl}-2,2,2-trifluoro-acetamide (123083-96-5)

Guidance literature:

Multi-step reaction with 11 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

With tetrahydrofuran; pyridine; 1H-imidazole; 2,6-dimethylpyridine; potassium hydroxide; 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) → N-{3-[(7E,11Z)-(1R,2S,4S,5R,6S,9R,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-13-hydroxy-1,4,5-trimethoxy-2,6,8,10-tetramethyl-trideca-7,11-dienyl]-2,5-dimethoxy-phenyl}-2,2,2-trifluoro-acetamide (123083-96-5)

Guidance literature:

Multi-step reaction with 13 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

With tetrahydrofuran; pyridine; 1H-imidazole; 2,6-dimethylpyridine; potassium hydroxide; lithium hydroxide; 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

upstream raw materials:

(2Z,6E)-(4S,5R,8S,9R,10S,12S,13R)-13-(3-Amino-2,5-dimethoxy-phenyl)-5-(tert-butyl-dimethyl-silanyloxy)-9,10,13-trimethoxy-4,6,8,12-tetramethyl-trideca-2,6-dien-1-ol

trifluoroacetic anhydride

t-butyldimethylsiyl triflate

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

Downstream 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

macbecin I

(2E,4Z,6S,7R,8E,10S,11R,12S,14S,15R)-15-(3-Amino-2,5-dimethoxyphenyl)-7-(tert-butyldimethylsiloxy)-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-2,4,8-pentadecatrienoic acid

(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