Acetic acid (3E,9E)-(1R,2R,5R,7S,11R,12S,14S,15R,16S)-16-benzyl-12-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-7,14-dimethyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.0^1,15]octadeca-3,9-dien-2-yl ester

Base Information

• Chemical Name: Acetic acid (3E,9E)-(1R,2R,5R,7S,11R,12S,14S,15R,16S)-16-benzyl-12-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-7,14-dimethyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.0^1,15]octadeca-3,9-dien-2-yl ester
• CAS No.: 127354-83-0
• Molecular Formula: C₃₅H₄₉NO₆Si
• Molecular Weight: 607.863

Synonyms:Acetic acid (3E,9E)-(1R,2R,5R,7S,11R,12S,14S,15R,16S)-16-benzyl-12-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-7,14-dimethyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.0^1,15]octadeca-3,9-dien-2-yl ester

Chemical Property of Acetic acid (3E,9E)-(1R,2R,5R,7S,11R,12S,14S,15R,16S)-16-benzyl-12-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-7,14-dimethyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.0^1,15]octadeca-3,9-dien-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (3E,9E)-(1R,2R,5R,7S,11R,12S,14S,15R,16S)-16-benzyl-12-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-7,14-dimethyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.0^1,15]octadeca-3,9-dien-2-yl ester

There total 10 articles about Acetic acid (3E,9E)-(1R,2R,5R,7S,11R,12S,14S,15R,16S)-16-benzyl-12-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-7,14-dimethyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.0^1,15]octadeca-3,9-dien-2-yl 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:

Acetic acid (3E,9E)-(1S,2S,5S,7R,11S,12R,14R,15S,16R)-17-acetyl-16-benzyl-12-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-7,14-dimethyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl ester (127354-82-9) → Acetic acid (3E,9E)-(1R,2R,5R,7S,11R,12S,14S,15R,16S)-16-benzyl-12-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-7,14-dimethyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl ester (127354-83-0)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; methanol; at -20 ℃; for 1.16667h;

DOI:10.1021/ja00167a037

Reference yield:

Acetic acid (E)-(1S,2S,3S,7R,11S,12R,14R,15S,16R)-17-acetyl-16-benzyl-12-(tert-butyl-dimethyl-silanyloxy)-7,14-dimethyl-13-methylene-3-methylsulfanyl-6,18-dioxo-17-aza-tricyclo[9.7.0.01,15]octadec-9-en-2-yl ester (127354-78-3) → Acetic acid (3E,9E)-(1R,2R,5R,7S,11R,12S,14S,15R,16S)-16-benzyl-12-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-7,14-dimethyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl ester (127354-83-0)

Guidance literature:

Multi-step reaction with 6 steps

1: DBU / acetonitrile / 12 h / 70 - 75 °C

2: CH₂Cl₂ / 0.17 h / -78 °C

3: MCPBA, NaHCO₃ / CH₂Cl₂ / 1.) -78 deg C, 35 min, 2.) from -78 deg C to -20 deg C, 35 min

4: CHCl₃ / 1.17 h / 50 °C

5: 53 percent / trimethylphosphite / propan-1-ol / 23 h / 100 - 105 °C

6: 0.7 mg / K₂CO₃ / tetrahydrofuran; methanol / 1.17 h / -20 °C

With sodium hydrogencarbonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; phosphorous acid trimethyl ester; In tetrahydrofuran; methanol; propan-1-ol; dichloromethane; chloroform; acetonitrile;

DOI:10.1021/ja00167a037

Reference yield:

Acetic acid (E)-(1R,2R,3S,7R,11R,14R,15S,16R)-17-acetyl-16-benzyl-7,14-dimethyl-3-methylsulfanyl-6,18-dioxo-13-phenylselanylmethyl-17-aza-tricyclo[9.7.0.01,15]octadeca-9,12-dien-2-yl ester (127354-76-1) → Acetic acid (3E,9E)-(1R,2R,5R,7S,11R,12S,14S,15R,16S)-16-benzyl-12-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-7,14-dimethyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl ester (127354-83-0)

Guidance literature:

Multi-step reaction with 8 steps

1: buffer solution pH 7, NaIO₄ / dioxane; H₂O / 1.17 h / Ambient temperature

2: imidazole, DMAP / dimethylformamide / 16 h / Ambient temperature

3: DBU / acetonitrile / 12 h / 70 - 75 °C

4: CH₂Cl₂ / 0.17 h / -78 °C

5: MCPBA, NaHCO₃ / CH₂Cl₂ / 1.) -78 deg C, 35 min, 2.) from -78 deg C to -20 deg C, 35 min

6: CHCl₃ / 1.17 h / 50 °C

7: 53 percent / trimethylphosphite / propan-1-ol / 23 h / 100 - 105 °C

8: 0.7 mg / K₂CO₃ / tetrahydrofuran; methanol / 1.17 h / -20 °C

With 1H-imidazole; dmap; sodium periodate; buffer solution pH 7; sodium hydrogencarbonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; phosphorous acid trimethyl ester; In tetrahydrofuran; 1,4-dioxane; methanol; propan-1-ol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00167a037

upstream raw materials:

Acetic acid (3E,9E)-(1S,2S,5S,7R,11S,12R,14R,15S,16R)-17-acetyl-16-benzyl-12-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-7,14-dimethyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.0^1,15]octadeca-3,9-dien-2-yl ester

Acetic acid (E)-(1S,2R,3S,7R,11S,14R,15S,16R)-17-acetyl-16-benzyl-12-hydroxy-7,14-dimethyl-13-methylene-3-methylsulfanyl-6,18-dioxo-17-aza-tricyclo[9.7.0.0^1,15]octadec-9-en-2-yl ester

Acetic acid (E)-(1R,2R,3S,7R,11R,14R,15S,16R)-17-acetyl-16-benzyl-7,14-dimethyl-3-methylsulfanyl-6,18-dioxo-13-phenylselanylmethyl-17-aza-tricyclo[9.7.0.0^1,15]octadeca-9,12-dien-2-yl ester

Acetic acid (E)-(1S,2S,3S,7R,11S,12R,14R,15S,16R)-17-acetyl-16-benzyl-12-(tert-butyl-dimethyl-silanyloxy)-7,14-dimethyl-13-methylene-3-methylsulfanyl-6,18-dioxo-17-aza-tricyclo[9.7.0.0^1,15]octadec-9-en-2-yl ester

Downstream raw materials:

dl-C₁₈-desmethylcytochalasin D

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