(4aR,9aR,10R)-8-Benzyloxy-10-hydroxy-10-methyl-4a,10-dihydro-4H,9aH-anthracene-1,9-dione

Base Information

• Chemical Name: (4aR,9aR,10R)-8-Benzyloxy-10-hydroxy-10-methyl-4a,10-dihydro-4H,9aH-anthracene-1,9-dione
• CAS No.: 82494-99-3
• Molecular Formula: C₂₂H₂₀O₄
• Molecular Weight: 348.398

Synonyms:(4aR,9aR,10R)-8-Benzyloxy-10-hydroxy-10-methyl-4a,10-dihydro-4H,9aH-anthracene-1,9-dione

Chemical Property of (4aR,9aR,10R)-8-Benzyloxy-10-hydroxy-10-methyl-4a,10-dihydro-4H,9aH-anthracene-1,9-dione

Chemical Property:

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Technology Process of (4aR,9aR,10R)-8-Benzyloxy-10-hydroxy-10-methyl-4a,10-dihydro-4H,9aH-anthracene-1,9-dione

There total 5 articles about (4aR,9aR,10R)-8-Benzyloxy-10-hydroxy-10-methyl-4a,10-dihydro-4H,9aH-anthracene-1,9-dione 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: 60.0%

(1S,4aR,9S,9aR,10R)-8-Benzyloxy-10-methyl-1,4,4a,9,9a,10-hexahydro-anthracene-1,9,10-triol (82495-03-2) → (4aR,9aR,10R)-8-Benzyloxy-10-hydroxy-10-methyl-4a,10-dihydro-4H,9aH-anthracene-1,9-dione (82494-99-3)

Guidance literature:

With jones reagent;

DOI:10.1021/jo00140a043

Reference yield:

(+/-)-4t-acetoxy-5,10t-dihydroxy-(4ar,9ac)-1,4,4a,9a-tetrahydro-anthrone (73794-50-0) → (4aR,9aR,10R)-8-Benzyloxy-10-hydroxy-10-methyl-4a,10-dihydro-4H,9aH-anthracene-1,9-dione (82494-99-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 54 percent / K₂CO₃

2: 74 percent

3: 85 percent / KOH / methanol

4: 60 percent / Jones reagent

With potassium hydroxide; jones reagent; potassium carbonate; In methanol;

DOI:10.1021/jo00140a043

Reference yield:

1-acetoxy-8-hydroxy-9,10-dioxo-1,4,4a,9,9a,10-hexahydroanthracene (73794-49-7) → (4aR,9aR,10R)-8-Benzyloxy-10-hydroxy-10-methyl-4a,10-dihydro-4H,9aH-anthracene-1,9-dione (82494-99-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 64 percent / LiAl(Bu^tO)3H

2: 54 percent / K₂CO₃

3: 74 percent

4: 85 percent / KOH / methanol

5: 60 percent / Jones reagent

With potassium hydroxide; jones reagent; potassium carbonate; lithium tri-t-butoxyaluminum hydride; In methanol;

DOI:10.1021/jo00140a043

upstream raw materials:

(1S,4aR,9S,9aR,10R)-8-Benzyloxy-10-methyl-1,4,4a,9,9a,10-hexahydro-anthracene-1,9,10-triol

(+/-)-4t-acetoxy-5,10t-dihydroxy-(4ar,9ac)-1,4,4a,9a-tetrahydro-anthrone

1-acetoxy-8-hydroxy-9,10-dioxo-1,4,4a,9,9a,10-hexahydroanthracene

10β-Hydroxy-4β-acetoxy-5-benzyloxy-9-oxo-1,4,4aα,9,9aα,10-hexahydro-anthracen

Downstream raw materials:

4,10-dioxo-4aβ-chloro-5-(benzyloxy)-9β-hydroxy-9α-methyl-1,4,9,9aα,10-pentahydroanthracene

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