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

Base Information

• Chemical Name: (4R,9R,10R)-(+)-4-(acetylamino)-9-(methoxycarbonyl)-cis-Δ⁶-1-octalone ethylene ketal
• CAS No.: 96246-11-6
• Molecular Formula: C₁₆H₂₃NO₅
• Molecular Weight: 309.362

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

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

Chemical Property:

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

There total 1 articles about (4R,9R,10R)-(+)-4-(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: 45.0%

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

Guidance literature:

With lithium methanolate; In methanol; at 0 - 25 ℃; for 4h;

DOI:10.1021/jo00211a024

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:

(4R,9R,10R)-(+)-4-(acetylamino)-9-(methoxycarbonyl)-cis-Δ6-1-octalone ethylene ketal (96246-11-6) → (4R,9R,10R)-4-(benzoylamino)-9-(methoxycarbonyl)-cis-Δ6-1-octalone ethylene ketal

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 15 h / 25 °C

2: 49 percent / LiOCH₃ / methanol / 4 h / 0 - 25 °C

With dmap; lithium methanolate; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jo00211a024

upstream raw materials:

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

Downstream raw materials:

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

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