(1R)-2α,5,7-Trihydroxy-2-methyl-6,11-dioxo-1,2,3,4,6,11-hexahydronaphthacene-1β-formic acid methyl ester

Base Information

• Chemical Name: (1R)-2α,5,7-Trihydroxy-2-methyl-6,11-dioxo-1,2,3,4,6,11-hexahydronaphthacene-1β-formic acid methyl ester
• CAS No.: 78173-93-0
• Molecular Formula: C₂₁H₁₈O₇
• Molecular Weight: 382.37
• Mol file: 78173-93-0.mol

Synonyms:(1R)-2α,5,7-Trihydroxy-2-methyl-6,11-dioxo-1,2,3,4,6,11-hexahydronaphthacene-1β-formic acid methyl ester;(1R,2R)-2-Methyl-1,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6,11-dioxo-1-naphthacenecarboxylic acid methyl ester;[1R,(+)]-1,2,3,4,6,11-Hexahydro-2α,5,7-trihydroxy-2-methyl-6,11-dioxo-1β-naphthacenecarboxylic acid methyl ester;4-Deoxyauramycinone;7-Deoxyauramycinone

Chemical Property of (1R)-2α,5,7-Trihydroxy-2-methyl-6,11-dioxo-1,2,3,4,6,11-hexahydronaphthacene-1β-formic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-2α,5,7-Trihydroxy-2-methyl-6,11-dioxo-1,2,3,4,6,11-hexahydronaphthacene-1β-formic acid methyl ester

There total 12 articles about (1R)-2α,5,7-Trihydroxy-2-methyl-6,11-dioxo-1,2,3,4,6,11-hexahydronaphthacene-1β-formic 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: 93.0%

(+/-)-7-deoxy-5,7-di-O-ethyl auramycinone (95455-52-0,95455-53-1) → (+/-)-7-deoxyauramycinone (78173-93-0,95530-32-8)

Guidance literature:

With aluminium trichloride; In dichloromethane; for 40h; Ambient temperature;

DOI:10.1016/S0040-4020(01)91536-4

Reference yield: 59.0%

(+/-)-4-O-methyl-7-deoxyauramycinone (95455-86-0,95455-88-2) → (+/-)-7-deoxyauramycinone (78173-93-0,95530-32-8)

Guidance literature:

With aluminium trichloride;

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

Reference yield:

1-(1-hydroxy-4,8-dimethoxynaphthalen-2-yl)ethanone (81418-41-9) → (+/-)-7-deoxyauramycinone (78173-93-0,95530-32-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 88 percent / NaH / tetrahydrofuran; dimethylformamide / 1.) RT, 1 h; 2.) RT, 3 h

2: 1.) lithium diisopropylamide

3: H₂ / Pd/C / tetrahydrofuran

4: p-toluenesulfonic acid / acetone; H₂O

5: 72 percent / ceric ammonium nitrate / H₂O; acetonitrile / 0.17 h / Ambient temperature

6: SnCl₄ / CH₂Cl₂ / 2 h / -20 °C

7: imidazole / dimethylformamide / 4 h / Ambient temperature

8: 35 percent / Kryptofix 222, HMPA, KH / tetrahydrofuran / 3 h / -78 - -50 °C

9: ceric ammonium nitrate

10: 1.) Br₂, AIBN; 2.) Et₃N, air

11: 59 percent / AlCl₃

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; aluminium trichloride; ammonium cerium(IV) nitrate; air; 2,2'-azobis(isobutyronitrile); hydrogen; bromine; tin(IV) chloride; potassium hydride; sodium hydride; toluene-4-sulfonic acid; triethylamine; [2.2.2]cryptande; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;

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

upstream raw materials:

(+/-)-4-O-methyl-7-deoxyauramycinone

(+/-)-7-deoxy-5,7-di-O-ethyl auramycinone

1-(1-hydroxy-4,8-dimethoxynaphthalen-2-yl)ethanone

5-methoxy-3-(5-oxohexanoyl)-1,4-naphthoquinone

Downstream raw materials:

(+/-)-auramycinone

Refernces

• 1、 Giesson,Jacquesy,Renoux. "A general and regiospecific route to tetracyclic alkenes in the 11-deoxyanthracyclinone series. Application to the total synthesis of (±)-auramycinone". . p. 4743 - 4750. Retrieved 2007/10/02.