(3R,6R,7S,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

Base Information

• Chemical Name: (3R,6R,7S,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine
• CAS No.: 1273048-06-8
• Molecular Formula: C₃₃H₃₂N₂O₅
• Molecular Weight: 536.627
• Mol file: 1273048-06-8.mol

Synonyms:(3R,6R,7S,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

Chemical Property of (3R,6R,7S,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,6R,7S,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

There total 4 articles about (3R,6R,7S,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 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: 48.0%

2-acetylindole (4264-35-1) + (3R,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-5-oxo-3-phenyl-3,5,8,8atetrahydro-5H-oxazolo[3,2-a]pyridine (1273047-82-7) → (3R,6R,7S,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (1273048-06-8) + (3R,6R,7R,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine + (3R,6S,7R,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

Guidance literature:

(3R,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-5-oxo-3-phenyl-3,5,8,8atetrahydro-5H-oxazolo[3,2-a]pyridine; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h;

2-acetylindole; In tetrahydrofuran; at -78 - 20 ℃; for 20h; optical yield given as %de;

DOI:10.1002/ejoc.201001020

Reference yield:

(3R,8R,8aS)-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (194149-77-4) → (3R,6R,7S,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (1273048-06-8) + (3R,6R,7R,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine + (3R,6S,7R,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -78 °C

1.2: 2 h / -78 °C

1.3: 2 h

2.1: ozone / dichloromethane / -78 - 25 °C

3.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C

3.2: 20 h / -78 - 20 °C

With ozone; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1002/ejoc.201001020

Reference yield:

(3R,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-5-oxo-3-phenyl-6-(phenylselenyl)-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (1273047-73-6) → (3R,6R,7S,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (1273048-06-8) + (3R,6R,7R,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine + (3R,6S,7R,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

Guidance literature:

Multi-step reaction with 2 steps

1.1: ozone / dichloromethane / -78 - 25 °C

2.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C

2.2: 20 h / -78 - 20 °C

With ozone; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1002/ejoc.201001020

upstream raw materials:

2-acetylindole

(3R,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-5-oxo-3-phenyl-3,5,8,8atetrahydro-5H-oxazolo[3,2-a]pyridine

(3R,8R,8aS)-6-(benzyloxycarbonyl)-8-ethyl-5-oxo-3-phenyl-6-(phenylselenyl)-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

benzyl chloroformate

Downstream raw materials:

(3R,7R,8R,8aS)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine