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

Base Information

• Chemical Name: 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
• CAS No.: 127354-77-2
• Molecular Formula: C₃₂H₄₁NO₆S
• Molecular Weight: 567.747

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 2 articles about 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 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 (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 (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[9.7.0.01,15]octadec-9-en-2-yl ester (127354-77-2)

Guidance literature:

With sodium periodate; buffer solution pH 7; In 1,4-dioxane; water; for 1.16667h; Yield given; Ambient temperature;

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-trimethylsilanylmethyl-17-aza-tricyclo[9.7.0.01,15]octadeca-9,12-dien-2-yl ester (116229-99-3,127354-75-0,127382-87-0) → 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[9.7.0.01,15]octadec-9-en-2-yl ester (127354-77-2)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / 0.08 h / -78 °C

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

With sodium periodate; buffer solution pH 7; In 1,4-dioxane; dichloromethane; water;

DOI:10.1021/ja00167a037

Reference yield:

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[9.7.0.01,15]octadec-9-en-2-yl ester (127354-77-2) → 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)

Guidance literature:

Multi-step reaction with 6 steps

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

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

3: CH₂Cl₂ / 0.17 h / -78 °C

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

5: CHCl₃ / 1.17 h / 50 °C

6: 53 percent / trimethylphosphite / propan-1-ol / 23 h / 100 - 105 °C

With 1H-imidazole; dmap; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; phosphorous acid trimethyl ester; In propan-1-ol; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00167a037

upstream raw materials:

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

Downstream raw materials:

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

dl-C₁₈-desmethylcytochalasin D

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

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

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