(1R)-6,11-Dioxo-2-ethyl-1,2,3,4,6,11-hexahydro-2α,5,7-trihydroxy-1β-naphthacenecarboxylic acid methyl ester

Base Information

• Chemical Name: (1R)-6,11-Dioxo-2-ethyl-1,2,3,4,6,11-hexahydro-2α,5,7-trihydroxy-1β-naphthacenecarboxylic acid methyl ester
• CAS No.: 21179-19-1
• Molecular Formula: C22H20O7
• Molecular Weight: 396.39
• Mol file: 21179-19-1.mol

Synonyms:7-Desoxyaklavinon;

Chemical Property of (1R)-6,11-Dioxo-2-ethyl-1,2,3,4,6,11-hexahydro-2α,5,7-trihydroxy-1β-naphthacenecarboxylic acid methyl ester

Chemical Property:

• PSA: 121.13000
• LogP: 2.21710

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R)-6,11-Dioxo-2-ethyl-1,2,3,4,6,11-hexahydro-2α,5,7-trihydroxy-1β-naphthacenecarboxylic acid methyl ester

There total 25 articles about (1R)-6,11-Dioxo-2-ethyl-1,2,3,4,6,11-hexahydro-2α,5,7-trihydroxy-1β-naphthacenecarboxylic acid methyl ester 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: 85.0%

methyl(9-RS,10-SR)-9-ethyl-6,9-dihydroxy-4-methoxy-5,12-dioxo-5,7,8,9,10,12-hexahydronaphthacene-10-carboxylate (80173-04-2,88365-19-9,97516-68-2,97516-69-3,137120-30-0) → t-2-Ethyl-1,2,3,4,6,11-hexahydro-c-2,5,7-trihydroxy-6,11-dioxo-r-1-naphthacencarbonsaeuremethylester (19260-55-0,21179-19-1,78821-96-2,80845-11-0,88391-19-9)

Guidance literature:

With aluminium trichloride;

DOI:10.1016/S0040-4020(01)91535-2

Reference yield: 26.0%

4,5-Dihydroxy-9,10-dioxo-3-(3-oxopentyl)anthracene-2-acetic Acid, Methyl Ester (74188-46-8) → methyl 9(R,S)-ethyl-4,6,9(R,S)-trihydroxy-5,12-dioxo-7,8,9,10-tetrahydronaphthacene-10(R,S)-carboxylate (78821-96-2) + t-2-Ethyl-1,2,3,4,6,11-hexahydro-c-2,5,7-trihydroxy-6,11-dioxo-r-1-naphthacencarbonsaeuremethylester (19260-55-0,21179-19-1,78821-96-2,80845-11-0,88391-19-9)

Guidance literature:

With pyridine; N-benzyl-trimethylammonium hydroxide; In methanol; 1) -15 deg C, 3 h, 2) to 8 deg C;

DOI:10.1021/jo00017a020

Reference yield:

1-formyl-butan-2-one ethylene acetal (76964-28-8) → t-2-Ethyl-1,2,3,4,6,11-hexahydro-c-2,5,7-trihydroxy-6,11-dioxo-r-1-naphthacencarbonsaeuremethylester (19260-55-0,21179-19-1,78821-96-2,80845-11-0,88391-19-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) lithium diisopropylamide / 1.) THF, -20 deg C, 30 min; 2) RT, 30 min, THF

2: 64 percent / H₂ / Pd/C / methanol

3: 93 percent / ceric ammonium nitrate / H₂O; acetonitrile / 0.17 h / Ambient temperature

4: 80 percent / SnCl₄ / CH₂Cl₂ / 2 h / -20 °C

5: imidazole / dimethylformamide / 4 h / Ambient temperature

6: 53 percent / Kryptofix 222, HMPA, KH / tetrahydrofuran / 3 h / -78 - -50 °C

7: ceric ammonium nitrate / H₂O; acetonitrile / 0.17 h / Ambient temperature

8: O₂ / dimethylformamide / 100 °C

9: 85 percent / AlCl₃

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; aluminium trichloride; ammonium cerium(IV) nitrate; hydrogen; oxygen; tin(IV) chloride; potassium hydride; [2.2.2]cryptande; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(01)91535-2

upstream raw materials:

4,5-Dihydroxy-9,10-dioxo-3-(3-oxopentyl)anthracene-2-acetic Acid, Methyl Ester

methyl(9-RS,10-SR)-9-ethyl-6,9-dihydroxy-4-methoxy-5,12-dioxo-5,7,8,9,10,12-hexahydronaphthacene-10-carboxylate

c-2-Ethyl-1,2,3,4,6,11-hexahydro-t-2,5-dihydroxy-7-methoxy-6,11-dioxo-r-1-naphthacencarbonsaeure-methylester

1-Hydroxy-3-(hydroxymethyl)-8-methoxy-2-(3-oxopentyl)-9,10-anthrachinon

Downstream raw materials:

Bisanhydroaklavinon

9-ethyl-4,6-dihydroxy-10-carbmethoxy-7,8-dihydro-5,12-naphthacenequinone

4,5-Dihydroxy-9,10-dioxo-3-(3-oxopentyl)anthracene-2-acetic Acid, Methyl Ester

t-2-Ethyl-1,2,3,4,6,11-hexahydro-c-2,t-4,5,7-tetrahydroxy-6,11-dioxo-r-1-naphthacencarbonsaeure-methylester