4,5α-epoxy-3-methoxy-17-methyl-7α-(4-phenyl-1,3-butadienyl)-6β,7β-(oxymethylene)morphinan

Base Information

Chemical Name:4,5α-epoxy-3-methoxy-17-methyl-7α-(4-phenyl-1,3-butadienyl)-6β,7β-(oxymethylene)morphinan
CAS No.:85454-97-3
Molecular Formula:C₂₉H₃₁NO₃
Molecular Weight:441.57
Hs Code.:

Synonyms:4,5α-epoxy-3-methoxy-17-methyl-7α-(4-phenyl-1,3-butadienyl)-6β,7β-(oxymethylene)morphinan

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Chemical Property of 4,5α-epoxy-3-methoxy-17-methyl-7α-(4-phenyl-1,3-butadienyl)-6β,7β-(oxymethylene)morphinan

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Technology Process of 4,5α-epoxy-3-methoxy-17-methyl-7α-(4-phenyl-1,3-butadienyl)-6β,7β-(oxymethylene)morphinan

There total 7 articles about 4,5α-epoxy-3-methoxy-17-methyl-7α-(4-phenyl-1,3-butadienyl)-6β,7β-(oxymethylene)morphinan 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:

: 77794-06-0
7,7-bis(hydroxymethyl)-4,5α-epoxy-3-methoxy-17-methylmorphinan-6β-ol hydrochloride

: 85454-97-3
4,5α-epoxy-3-methoxy-17-methyl-7α-(4-phenyl-1,3-butadienyl)-6β,7β-(oxymethylene)morphinan

Guidance literature:: Multi-step reaction with 6 steps

1: 13 percent / pyridine / Ambient temperature

2: 73 percent / 1N NaOH / butan-2-one / 2 h / Heating

3: 97 percent / dimethylformamide / 18 h / 100 °C

4: 66 percent / NaOMe / methanol / 0.5 h

5: 72 percent / 1.) TFAA*Me₂SO, 2.) TEA / CH₂Cl₂ / 1.5 h / -60 °C

6: 1.) NaH / 1.) DMSO, 25 deg C, 10 min, 2.) DMSO, room temp., 30 min, 65-70 deg C, 30 min

With sodium hydroxide; TEA; sodium methylate; sodium hydride; trifluoroacetic anhydride; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; butanone;
DOI:10.1021/jo00159a005

Reference yield:

: 77794-00-4
7,7-bis<(tosyloxy)methyl>-4,5α-epoxy-3-methoxy-17-methylmorphinan-6β-ol

: 85454-97-3
4,5α-epoxy-3-methoxy-17-methyl-7α-(4-phenyl-1,3-butadienyl)-6β,7β-(oxymethylene)morphinan

Guidance literature:: Multi-step reaction with 5 steps

1: 73 percent / 1N NaOH / butan-2-one / 2 h / Heating

2: 97 percent / dimethylformamide / 18 h / 100 °C

3: 66 percent / NaOMe / methanol / 0.5 h

4: 72 percent / 1.) TFAA*Me₂SO, 2.) TEA / CH₂Cl₂ / 1.5 h / -60 °C

5: 1.) NaH / 1.) DMSO, 25 deg C, 10 min, 2.) DMSO, room temp., 30 min, 65-70 deg C, 30 min

With sodium hydroxide; TEA; sodium methylate; sodium hydride; trifluoroacetic anhydride; In methanol; dichloromethane; N,N-dimethyl-formamide; butanone;
DOI:10.1021/jo00159a005

Reference yield:

: 85454-95-1
4,5α-epoxy-7α-(hydroxymethyl)-3-methoxy-17-methyl-6β,7β-(oxymethylene)morphinan

: 85454-97-3
4,5α-epoxy-3-methoxy-17-methyl-7α-(4-phenyl-1,3-butadienyl)-6β,7β-(oxymethylene)morphinan

Guidance literature:: Multi-step reaction with 2 steps

1: 72 percent / 1.) TFAA*Me₂SO, 2.) TEA / CH₂Cl₂ / 1.5 h / -60 °C

2: 1.) NaH / 1.) DMSO, 25 deg C, 10 min, 2.) DMSO, room temp., 30 min, 65-70 deg C, 30 min

With TEA; sodium hydride; trifluoroacetic anhydride; In dichloromethane;
DOI:10.1021/jo00159a005