[3R,(-)]-6β-Acetyloxy-2,3,5aβ,6,11,11a-hexahydro-3α,11aα-bis(methylthio)-3-benzyloxepino[3',4':4,5]pyrrolo[1,2-a]pyrazine-1,4-dione

Base Information

• Chemical Name: [3R,(-)]-6β-Acetyloxy-2,3,5aβ,6,11,11a-hexahydro-3α,11aα-bis(methylthio)-3-benzyloxepino[3',4':4,5]pyrrolo[1,2-a]pyrazine-1,4-dione
• CAS No.: 106010-20-2
• Molecular Formula: C₂₂H₂₄N₂O₅S₂
• Molecular Weight: 460.575
• Mol file: 106010-20-2.mol

Synonyms:Oxepino[3',4':4,5]pyrrolo[1,2-a]pyrazine-1,4-dione,6-(acetyloxy)-2,3,5a,6,11,11a-hexahydro-3,11a-bis(methylthio)-3-(phenylmethyl)-,[3R-(3a,5ab,6b,11aa)]-; Asteroxepin

Chemical Property of [3R,(-)]-6β-Acetyloxy-2,3,5aβ,6,11,11a-hexahydro-3α,11aα-bis(methylthio)-3-benzyloxepino[3',4':4,5]pyrrolo[1,2-a]pyrazine-1,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [3R,(-)]-6β-Acetyloxy-2,3,5aβ,6,11,11a-hexahydro-3α,11aα-bis(methylthio)-3-benzyloxepino[3',4':4,5]pyrrolo[1,2-a]pyrazine-1,4-dione

There total 12 articles about [3R,(-)]-6β-Acetyloxy-2,3,5aβ,6,11,11a-hexahydro-3α,11aα-bis(methylthio)-3-benzyloxepino[3',4':4,5]pyrrolo[1,2-a]pyrazine-1,4-dione 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: 89.0%

(-)-emestrin H + acetic anhydride (108-24-7) → (-)-asteroxepin (106010-20-2)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 2.16667h; Inert atmosphere;

DOI:10.1016/j.tet.2020.131630

Reference yield:

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) → (-)-asteroxepin (106010-20-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: triethylamine; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride / dichloromethane / 2.7 h / 20 °C / Inert atmosphere

2.1: triethylamine; palladium diacetate / dichloromethane / 0.5 h / Reflux; Inert atmosphere

2.2: 0.67 h / Reflux; Inert atmosphere

3.1: ammonium hydroxide / methanol / 64.8 h / 20 °C / Inert atmosphere

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.13 h / -40 °C / Inert atmosphere

4.2: 17 h / -20 °C / Inert atmosphere

5.1: pyridine hydrofluoride / pyridine / 17 h / 45 °C / Inert atmosphere

6.1: [bis(acetoxy)iodo]benzene; 9-benzyl-9-norazaadamantane N-oxyl / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

7.1: cerium(III) chloride heptahydrate / dichloromethane; ethanol / 0.17 h / -78 °C / Inert atmosphere

7.2: 1.6 h / -78 °C / Inert atmosphere

8.1: lithium hexamethyldisilazane; sulfur / tetrahydrofuran; diethyl ether / 0.52 h / 20 °C / Inert atmosphere

8.2: 0.13 h / 20 °C / Inert atmosphere

9.1: tetrahydrofuran; ethanol / 4 h / 20 °C / Inert atmosphere

10.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-dimethylbarbituric acid; methanol / 18.5 h / 40 °C / Inert atmosphere

11.1: dmap; pyridine / 2.17 h / 20 °C / Inert atmosphere

With pyridine; methanol; sulfur; dmap; ammonium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-dimethylbarbituric acid; 9-benzyl-9-norazaadamantane N-oxyl; pyridine hydrofluoride; [bis(acetoxy)iodo]benzene; cerium(III) chloride heptahydrate; palladium diacetate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; 7.1: |Luche Cerium Reduction / 7.2: |Luche Cerium Reduction;

DOI:10.1016/j.tet.2020.131630

Reference yield:

C33H42N2O7Si → (-)-asteroxepin (106010-20-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: triethylamine; palladium diacetate / dichloromethane / 0.5 h / Reflux; Inert atmosphere

1.2: 0.67 h / Reflux; Inert atmosphere

2.1: ammonium hydroxide / methanol / 64.8 h / 20 °C / Inert atmosphere

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.13 h / -40 °C / Inert atmosphere

3.2: 17 h / -20 °C / Inert atmosphere

4.1: pyridine hydrofluoride / pyridine / 17 h / 45 °C / Inert atmosphere

5.1: [bis(acetoxy)iodo]benzene; 9-benzyl-9-norazaadamantane N-oxyl / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

6.1: cerium(III) chloride heptahydrate / dichloromethane; ethanol / 0.17 h / -78 °C / Inert atmosphere

6.2: 1.6 h / -78 °C / Inert atmosphere

7.1: lithium hexamethyldisilazane; sulfur / tetrahydrofuran; diethyl ether / 0.52 h / 20 °C / Inert atmosphere

7.2: 0.13 h / 20 °C / Inert atmosphere

8.1: tetrahydrofuran; ethanol / 4 h / 20 °C / Inert atmosphere

9.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-dimethylbarbituric acid; methanol / 18.5 h / 40 °C / Inert atmosphere

10.1: dmap; pyridine / 2.17 h / 20 °C / Inert atmosphere

With pyridine; methanol; sulfur; dmap; ammonium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-dimethylbarbituric acid; 9-benzyl-9-norazaadamantane N-oxyl; pyridine hydrofluoride; [bis(acetoxy)iodo]benzene; cerium(III) chloride heptahydrate; palladium diacetate; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; 6.1: |Luche Cerium Reduction / 6.2: |Luche Cerium Reduction;

DOI:10.1016/j.tet.2020.131630

upstream raw materials:

methyl (2S)-2-amino-3-phenylpropanoate

(2S,8R,8aS)-1-((benzyloxy)carbonyl)-8-((tert-butyldimethylsilyl)oxy)-2,3,8,8a-tetrahydro-1H-oxepino[4,3-b]pyrrole-2-carboxylic acid

acetic anhydride

Refernces