18R-benzyloxy-4,5α-epoxy-7α-hydroxymethyl-3-methoxy-17-methyl-6α,14α-ethano-isomorphinan

Base Information

• Chemical Name: 18R-benzyloxy-4,5α-epoxy-7α-hydroxymethyl-3-methoxy-17-methyl-6α,14α-ethano-isomorphinan
• CAS No.: 848252-07-3
• Molecular Formula: C₂₉H₃₅NO₅
• Molecular Weight: 477.601
• Mol file: 848252-07-3.mol

Synonyms:18R-benzyloxy-4,5α-epoxy-7α-hydroxymethyl-3-methoxy-17-methyl-6α,14α-ethano-isomorphinan

Chemical Property of 18R-benzyloxy-4,5α-epoxy-7α-hydroxymethyl-3-methoxy-17-methyl-6α,14α-ethano-isomorphinan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 18R-benzyloxy-4,5α-epoxy-7α-hydroxymethyl-3-methoxy-17-methyl-6α,14α-ethano-isomorphinan

There total 2 articles about 18R-benzyloxy-4,5α-epoxy-7α-hydroxymethyl-3-methoxy-17-methyl-6α,14α-ethano-isomorphinan 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: 31.0%

4,5α-epoxy-18R-hydroxy-7α-hydroxymethyl-3-methoxy-17-methyl-6α,14α-ethano-isomorphinan (848252-03-9) + benzyl bromide (100-39-0) → 18R-benzyloxy-4,5α-epoxy-7α-hydroxymethyl-3-methoxy-17-methyl-6α,14α-ethano-isomorphinan (848252-07-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at -78 - 60 ℃; for 1h;

DOI:10.1021/jo048388u

Reference yield:

7α-methoxycarbonyl-6,14-endo-etheno-6,7,8,14-tetrahydrothebaine (16193-33-2) → 18R-benzyloxy-4,5α-epoxy-7α-hydroxymethyl-3-methoxy-17-methyl-6α,14α-ethano-isomorphinan (848252-07-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BH₃*Me₂S / tetrahydrofuran / 5.5 h / 20 - 70 °C

1.2: 46 percent / NaOH; H₂O₂ / H₂O; tetrahydrofuran

2.1: 31 percent / NaH / dimethylformamide / 1 h / -78 - 60 °C

With dimethylsulfide borane complex; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo048388u

Reference yield: 78.0%

18R-benzyloxy-4,5α-epoxy-7α-hydroxymethyl-3-methoxy-17-methyl-6α,14α-ethano-isomorphinan (848252-07-3) → 18R-benzyloxy-7α-carboxaldehydo-4,5α-epoxy-3-methoxy-17-methyl-6α,14α-ethano-isomorphinan

Guidance literature:

With Dess-Martin periodane; In dichloromethane; water;

DOI:10.1021/jo048388u

upstream raw materials:

4,5α-epoxy-18R-hydroxy-7α-hydroxymethyl-3-methoxy-17-methyl-6α,14α-ethano-isomorphinan

benzyl bromide

7α-methoxycarbonyl-6,14-endo-etheno-6,7,8,14-tetrahydrothebaine

Refernces