7-Deoxypyrromycinone

Base Information

• Chemical Name: 7-Deoxypyrromycinone
• CAS No.: 21179-18-0
• Molecular Formula: C₂₂H₂₀O₈
• Molecular Weight: 412.396
• Mol file: 21179-18-0.mol

Synonyms:(1R,2R)-2-Ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester;(1R)-2c-Aethyl-2t,5,7,10-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1r-carbonsaeure-methylester;

Chemical Property of 7-Deoxypyrromycinone

Chemical Property:

• Vapor Pressure: 1.34E-17mmHg at 25°C
• Boiling Point: 646.6°C at 760 mmHg
• Flash Point: 228.6°C
• PSA: 141.36000
• Density: 1.517g/cm³
• LogP: 1.92270

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 7-Deoxypyrromycinone

There total 23 articles about 7-Deoxypyrromycinone 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: 94.0%

10(R,S)-(methoxycarbonyl)-9(R,S)-ethyl-9(R,S)-hydroxy-7,8,9,10-tetrahydro-1,4,6-trimethoxy-5,12-naphthacenedione (88453-81-0,88453-82-1) → (+/-)-ε-deoxypyrromycinone (641-92-9,21179-18-0,88495-24-3)

Guidance literature:

With aluminium trichloride; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1021/ja00316a048

Reference yield:

methyl 2-<3-(3-(benzyloxy)pent-1-yl)-5,8-dimethoxy-4-hydroxyanthraquinon-2-yl>acetate (88453-73-0) → (+/-)-ε-deoxypyrromycinone (641-92-9,21179-18-0,88495-24-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / 1.) potassium carbonate, 2.) triethylamine / 1.) acetone, reflux, 8 h, 2.) ethyl acetate, r.t., 0.5 h

2: 93 percent / hydrochloride acid, H₂ / 10percent Pd/C / methanol / 1 h / 1137.7 Torr / Ambient temperature

3: 93 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

4: 156 mg / magnesium methoxide / methanol / 5 h / Ambient temperature

5: 94 percent / aluminium chloride / CH₂Cl₂ / 2 h / Ambient temperature

With hydrogenchloride; aluminium trichloride; hydrogen; potassium carbonate; magnesium methanolate; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/ja00316a048

Reference yield:

methyl <3-(3-(benzyloxy)pent-1-yl)-4,5,8-trimethoxyanthraquinon-2-yl>acetate (88453-75-2) → (+/-)-ε-deoxypyrromycinone (641-92-9,21179-18-0,88495-24-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / hydrochloride acid, H₂ / 10percent Pd/C / methanol / 1 h / 1137.7 Torr / Ambient temperature

2: 93 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

3: 156 mg / magnesium methoxide / methanol / 5 h / Ambient temperature

4: 94 percent / aluminium chloride / CH₂Cl₂ / 2 h / Ambient temperature

With hydrogenchloride; aluminium trichloride; hydrogen; magnesium methanolate; pyridinium chlorochromate; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/ja00316a048

upstream raw materials:

7,10-di-O-methyl-ξ-pyrromycinone

10(R,S)-(methoxycarbonyl)-9(R,S)-ethyl-9(R,S)-hydroxy-7,8,9,10-tetrahydro-1,4,6-trimethoxy-5,12-naphthacenedione

methyl <3-(3-hydroxypent-1-yl)-4,5,8-trimethoxyanthraquinon-2-yl>acetate

methyl <3-(3-oxopent-1-yl)-4,5,8-trimethoxyanthraquinon-2-yl>acetate

Downstream raw materials:

(+/-)-ε-pyrromycinone

Refernces

• 1、 Krohn, Karsten,Klimars, Michael,Koehle, Hans-Juergen,Ebeling, Eckehardt. "SYNTHESIS OF ξ-PYRROMYCINONE, 7-DEOXYAURAMYCINONE, AND 7-DEOXYAKLAVINONE VIA KETOESTER CYCLIZATION". . p. 3677 - 3694. Retrieved 2007/10/02.