(4R,9R,10R)-4-(N-benzoyl-N-acetylamino)-9-(methoxycarbonyl)-cis-Δ⁶-1-octalone ethylene ketal

Base Information

• Chemical Name: (4R,9R,10R)-4-(N-benzoyl-N-acetylamino)-9-(methoxycarbonyl)-cis-Δ⁶-1-octalone ethylene ketal
• CAS No.: 96246-27-4
• Molecular Formula: C₂₃H₂₇NO₆
• Molecular Weight: 413.47

Synonyms:(4R,9R,10R)-4-(N-benzoyl-N-acetylamino)-9-(methoxycarbonyl)-cis-Δ⁶-1-octalone ethylene ketal

Chemical Property of (4R,9R,10R)-4-(N-benzoyl-N-acetylamino)-9-(methoxycarbonyl)-cis-Δ⁶-1-octalone ethylene ketal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,9R,10R)-4-(N-benzoyl-N-acetylamino)-9-(methoxycarbonyl)-cis-Δ⁶-1-octalone ethylene ketal

There total 10 articles about (4R,9R,10R)-4-(N-benzoyl-N-acetylamino)-9-(methoxycarbonyl)-cis-Δ⁶-1-octalone ethylene ketal 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: 96.0%

benzoyl chloride (98-88-4) + (4R,9R,10R)-(+)-4-(acetylamino)-9-(methoxycarbonyl)-cis-Δ6-1-octalone ethylene ketal (96246-11-6) → (4R,9R,10R)-4-(N-benzoyl-N-acetylamino)-9-(methoxycarbonyl)-cis-Δ6-1-octalone ethylene ketal (96246-27-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 25 ℃; for 15h;

DOI:10.1021/jo00211a024

Reference yield:

(1R,4aR,8aS)-1-(1-Bromo-1-methyl-ethyl)-4-oxo-1,3,4,5,8,8a-hexahydro-2H-naphthalene-4a-carboxylic acid ethyl ester (96246-15-0) → (4R,9R,10R)-4-(N-benzoyl-N-acetylamino)-9-(methoxycarbonyl)-cis-Δ6-1-octalone ethylene ketal (96246-27-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 62 percent / (i-Pr)2NEt / dioxane / 66 h / 60 - 65 °C

2: 91 percent / p-toluenesulfonic acid / benzene / 6 h / Heating

3: 91 percent / EtSLi, HMPA / 2.5 h / 100 °C

4: 1.) NaHCO₃, 2.) KI, I₂ / 1.) THF, H₂O, 0 deg C, 15 min, 2.) THF, H₂O, 25 deg C, 20 h

5: 1.) O₃, O₂, 2.) Me₂S / 1.) CH₃OH, -78 deg C, 2.) CH₃OH, a) from -78 deg C to 25 deg C, 3 h, b) 25 deg C, 12 h

6: hydroxylamine hydrochloride, 4-(dimethylamino)pyridine, pyridine / methanol / 18 h / 25 °C

7: Et₃N / CH₂Cl₂ / 1 h / -20 - -15 °C

8: SiO₂, chloroform / 42 h

9: Zn / ethanol / 1.25 h / 70 °C

10: methanol; diethyl ether / 3 h / 0 - 25 °C

11: 96 percent / 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 15 h / 25 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; dimethylsulfide; chloroform; hydroxylamine hydrochloride; iodine; oxygen; silica gel; sodium hydrogencarbonate; lithium thioethoxide; toluene-4-sulfonic acid; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; potassium iodide; zinc; In 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; benzene;

DOI:10.1021/jo00211a024

Reference yield:

(4R,9R,10S)-(+)-9-(ethoxycarbonyl)-4-(2-propenyl)-cis-Δ6-1-octalone (96246-16-1) → (4R,9R,10R)-4-(N-benzoyl-N-acetylamino)-9-(methoxycarbonyl)-cis-Δ6-1-octalone ethylene ketal (96246-27-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 91 percent / p-toluenesulfonic acid / benzene / 6 h / Heating

2: 91 percent / EtSLi, HMPA / 2.5 h / 100 °C

3: 1.) NaHCO₃, 2.) KI, I₂ / 1.) THF, H₂O, 0 deg C, 15 min, 2.) THF, H₂O, 25 deg C, 20 h

4: 1.) O₃, O₂, 2.) Me₂S / 1.) CH₃OH, -78 deg C, 2.) CH₃OH, a) from -78 deg C to 25 deg C, 3 h, b) 25 deg C, 12 h

5: hydroxylamine hydrochloride, 4-(dimethylamino)pyridine, pyridine / methanol / 18 h / 25 °C

6: Et₃N / CH₂Cl₂ / 1 h / -20 - -15 °C

7: SiO₂, chloroform / 42 h

8: Zn / ethanol / 1.25 h / 70 °C

9: methanol; diethyl ether / 3 h / 0 - 25 °C

10: 96 percent / 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 15 h / 25 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; dimethylsulfide; chloroform; hydroxylamine hydrochloride; iodine; oxygen; silica gel; sodium hydrogencarbonate; lithium thioethoxide; toluene-4-sulfonic acid; ozone; triethylamine; potassium iodide; zinc; In methanol; diethyl ether; ethanol; dichloromethane; benzene;

DOI:10.1021/jo00211a024

upstream raw materials:

benzoyl chloride

(4R,9R,10R)-(+)-4-(acetylamino)-9-(methoxycarbonyl)-cis-Δ⁶-1-octalone ethylene ketal

(4R,9R,10S)-(+)-9-(ethoxycarbonyl)-4-(2-propenyl)-cis-Δ⁶-1-octalone

(1R,4aR,8aS)-1-(1-Bromo-1-methyl-ethyl)-4-oxo-1,3,4,5,8,8a-hexahydro-2H-naphthalene-4a-carboxylic acid ethyl ester

Downstream raw materials:

(4R,9R,10R)-(+)-4-(acetylamino)-9-(methoxycarbonyl)-cis-Δ⁶-1-octalone ethylene ketal

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