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

Base Information

• Chemical Name: 7,7-bis<(tosyloxy)methyl>-4,5α-epoxy-3-methoxy-17-methylmorphinan-6α-ol
• CAS No.: 85455-01-2
• Molecular Formula: C₃₄H₃₉NO₉S₂
• Molecular Weight: 669.817

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

Chemical Property of 7,7-bis<(tosyloxy)methyl>-4,5α-epoxy-3-methoxy-17-methylmorphinan-6α-ol

Chemical Property:

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Technology Process of 7,7-bis<(tosyloxy)methyl>-4,5α-epoxy-3-methoxy-17-methylmorphinan-6α-ol

There total 2 articles about 7,7-bis<(tosyloxy)methyl>-4,5α-epoxy-3-methoxy-17-methylmorphinan-6α-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:

7,7-bis<(tosyloxy)methyl>-4,5α-epoxy-3-methoxy-17-methylmorphinan-6-one (85455-00-1) → 7,7-bis<(tosyloxy)methyl>-4,5α-epoxy-3-methoxy-17-methylmorphinan-6α-ol (85455-01-2)

Guidance literature:

With sodium tetrahydroborate; In ethanol; chloroform; for 1.5h; Yield given;

DOI:10.1021/jo00159a005

Reference yield:

7,7-bis<(tosyloxy)methyl>-4,5α-epoxy-3-methoxy-17-methylmorphinan-6β-ol (77794-00-4) → 7,7-bis<(tosyloxy)methyl>-4,5α-epoxy-3-methoxy-17-methylmorphinan-6α-ol (85455-01-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / 1.) TFAA*Me₂SO, 2.) TEA / CH₂Cl₂ / 1.5 h / -60 °C

2: NaBH₄ / ethanol; CHCl₃ / 1.5 h

With sodium tetrahydroborate; TEA; trifluoroacetic anhydride; In ethanol; dichloromethane; chloroform;

DOI:10.1021/jo00159a005

Reference yield: 93.0%

7,7-bis<(tosyloxy)methyl>-4,5α-epoxy-3-methoxy-17-methylmorphinan-6α-ol (85455-01-2) → 4,5α-epoxy-3-methoxy-17-methyl-7β-<(tosyloxy)methyl>-6β,7β-(oxymethylene)morphinan (85455-02-3)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 65 - 70 ℃; for 1h;

DOI:10.1021/jo00159a005

upstream raw materials:

7,7-bis<(tosyloxy)methyl>-4,5α-epoxy-3-methoxy-17-methylmorphinan-6-one

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

Downstream raw materials:

4,5α-epoxy-3-methoxy-17-methyl-7β-<(tosyloxy)methyl>-6β,7β-(oxymethylene)morphinan

7α,17-dimethyl-4,5α-epoxy-3-methoxy-7β-(4-phenylbutyl)morphinan-6α-ol

C₂₈H₃₄BrNO₃

4,5α-epoxy-17-methyl-7β-(4-phenylbutyl)-6α,7α-(oxymethylene)morphinan-3-ol

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