(14S)-3,6-Dimethoxy-7beta-acetyl-17-methyl-4,5alpha-epoxy-6alpha,14-ethanomorphinan

Base Information

• Chemical Name: (14S)-3,6-Dimethoxy-7beta-acetyl-17-methyl-4,5alpha-epoxy-6alpha,14-ethanomorphinan
• CAS No.: 16196-83-1
• Molecular Formula: C₂₃H₂₉NO₄
• Molecular Weight: 383.488
• DSSTox Substance ID: DTXSID101116291
• Nikkaji Number: J637.466B
• Mol file: 16196-83-1.mol

Synonyms:DTXSID101116291;(14S)-3,6-Dimethoxy-7beta-acetyl-17-methyl-4,5alpha-epoxy-6alpha,14-ethanomorphinan;16196-83-1;Ethanone, 1-[(5alpha,7beta)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-17-methyl-6,14-ethenomorphinan-7-yl]-

Chemical Property of (14S)-3,6-Dimethoxy-7beta-acetyl-17-methyl-4,5alpha-epoxy-6alpha,14-ethanomorphinan

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 383.20965841
• Heavy Atom Count: 28
• Complexity: 713

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)C1CC23CCC1(C4C25CCN(C3CC6=C5C(=C(C=C6)OC)O4)C)OC
• Isomeric SMILES: CC(=O)[C@@H]1C[C@@]23CC[C@@]1([C@H]4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)OC)O4)C)OC

Technology Process of (14S)-3,6-Dimethoxy-7beta-acetyl-17-methyl-4,5alpha-epoxy-6alpha,14-ethanomorphinan

There total 2 articles about (14S)-3,6-Dimethoxy-7beta-acetyl-17-methyl-4,5alpha-epoxy-6alpha,14-ethanomorphinan 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:

C23H27NO4 → 7-acetyl-6,14-endo-ethano-6,7,8,14-tetrahydrothebaine (16196-82-0) + 7α-acetyl-6,14-endoethanotetrahydrothebaine (16196-83-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In toluene; at 55 ℃; under 4500.4 Torr;

DOI:10.1080/00397919508013419

Reference yield:

→ 1-(4,5-epoxy-3,6-dimethoxy-17-methyl-6,14-ethano-morphinan-7-yl)-ethanone (16196-82-0,16196-83-1,22152-79-0,137942-74-6)

Guidance literature:

Reference yield:

tertiary butyl chloride (507-20-0) + 7α-acetyl-6,14-endoethanotetrahydrothebaine (16196-83-1) → [5α,7α]-α-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-α,17-dimethyl-6,14-ethenomorphinan-7-methanol (22152-80-3,85080-82-6,98301-16-7,98301-77-0,136232-78-5,136314-59-5,16196-70-6)

Guidance literature:

tertiary butyl chloride; With magnesium; In tetrahydrofuran; cyclohexane; at 64 - 74 ℃;

7α-acetyl-6,14-endoethanotetrahydrothebaine; In tetrahydrofuran; cyclohexane; at 8 - 12 ℃; for 1h;

Downstream raw materials:

7-acetyl-6,14-endo-ethano-6,7,8,14-tetrahydrothebaine

[5α,7α]-α-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-α,17-dimethyl-6,14-ethenomorphinan-7-methanol

Buprenorphine

buprenorphine hydrochloride