4,5α-epoxy-19anti-((S)-1-hydroxy-1-phenyl-ethyl)-6-methoxy-17-methyl-8β,14-ethano-morphin-7-en-3-ol

Base Information

• Chemical Name: 4,5α-epoxy-19anti-((S)-1-hydroxy-1-phenyl-ethyl)-6-methoxy-17-methyl-8β,14-ethano-morphin-7-en-3-ol
• CAS No.: 16609-85-1
• Molecular Formula: C₂₈H₃₁NO₄
• Molecular Weight: 445.558

Synonyms:4,5α-epoxy-19anti-((S)-1-hydroxy-1-phenyl-ethyl)-6-methoxy-17-methyl-8β,14-ethano-morphin-7-en-3-ol

Chemical Property of 4,5α-epoxy-19anti-((S)-1-hydroxy-1-phenyl-ethyl)-6-methoxy-17-methyl-8β,14-ethano-morphin-7-en-3-ol

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Technology Process of 4,5α-epoxy-19anti-((S)-1-hydroxy-1-phenyl-ethyl)-6-methoxy-17-methyl-8β,14-ethano-morphin-7-en-3-ol

There total 2 articles about 4,5α-epoxy-19anti-((S)-1-hydroxy-1-phenyl-ethyl)-6-methoxy-17-methyl-8β,14-ethano-morphin-7-en-3-ol 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: 50.0%

(5R,6R,7R,9R,13S,14R,20S)-4,5-Epoxy-3,6-dimethoxy-α,17-dimethyl-α-phenyl-6,14-ethenomorphinan-7-methanol (16180-37-3) → 4,5α-epoxy-19anti-((S)-1-hydroxy-1-phenyl-ethyl)-6-methoxy-17-methyl-8β,14-ethano-morphin-7-en-3-ol (16609-85-1)

Guidance literature:

With potassium hydroxide; In diethylene glycol; at 210 - 220 ℃; for 1.5h;

DOI:10.1016/S0968-0896(96)00257-X

Reference yield:

nepenthone (464-66-4) → 4,5α-epoxy-19anti-((S)-1-hydroxy-1-phenyl-ethyl)-6-methoxy-17-methyl-8β,14-ethano-morphin-7-en-3-ol (16609-85-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / toluene; tetrahydrofuran / 1 h / Heating

2: 50 percent / KOH / bis-(2-hydroxy-ethyl) ether / 1.5 h / 210 - 220 °C

With potassium hydroxide; In tetrahydrofuran; toluene; diethylene glycol;

DOI:10.1016/S0968-0896(96)00257-X

Reference yield:

4,5α-epoxy-19anti-((S)-1-hydroxy-1-phenyl-ethyl)-6-methoxy-17-methyl-8β,14-ethano-morphin-7-en-3-ol (16609-85-1) → (S)-1-(4,5α-epoxy-6-methoxy-17-methyl-8α,14α-etheno-morphinan-7α-yl)-1-phenyl-ethanol (26632-74-6)

Guidance literature:

Multistep reaction; (i) HOP(OEt)2, Et₃N, CCl₄, (ii) Na, liq. NH₃, Et₂O;

DOI:10.1021/jm00297a041

upstream raw materials:

(5R,6R,7R,9R,13S,14R,20S)-4,5-Epoxy-3,6-dimethoxy-α,17-dimethyl-α-phenyl-6,14-ethenomorphinan-7-methanol

nepenthone

Downstream raw materials:

(S)-1-(4,5α-epoxy-6-methoxy-17-methyl-8α,14α-etheno-morphinan-7α-yl)-1-phenyl-ethanol

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