beta-Rhodomycinone

Base Information

• Chemical Name: beta-Rhodomycinone
• CAS No.: 5012-65-7
• Molecular Formula: C₂₀H₁₈O₈
• Molecular Weight: 386.358
• Mol file: 5012-65-7.mol

Synonyms:5,12-Naphthacenedione,8-ethyl-7,8,9,10-tetrahydro-1,6,7,8,10,11-hexahydroxy-, [7R-(7a,8b,10b)]-; b-Rhodomycinone (7CI)

Chemical Property of beta-Rhodomycinone

Chemical Property:

• Vapor Pressure: 3.75E-14mmHg at 25°C
• Boiling Point: 577°Cat760mmHg
• Flash Point: 316.8°C
• PSA: 155.52000
• Density: 1.693g/cm³
• LogP: 1.19040

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of beta-Rhodomycinone

There total 8 articles about beta-Rhodomycinone 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:

Trifluoro-acetic acid (1R,2R)-4-bromo-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yl ester → β-Rhodomycinone (5012-65-7) + 10-O-trifluoroacetyl-β-rhodomycinone (121878-73-7)

Guidance literature:

With sodium hydrogencarbonate; In diethyl ether; at 5 ℃; for 0.25h; Yield given. Title compound not separated from byproducts;

DOI:10.1248/cpb.40.61

Reference yield:

10-O-trifluoroacetyl-γ-rhodomycinone (17514-34-0) → β-Rhodomycinone (5012-65-7)

Guidance literature:

Multi-step reaction with 2 steps

1: Br₂ / CCl₄ / 0.5 h / Irradiation

2: 1.) 0.1 N NaHCO₃, 2.) 0.1 N NaOH / 1.) Et₂O, 5 deg C, 15 min, 2.) Et₂O, 5 deg C, 5 min

With sodium hydroxide; bromine; sodium hydrogencarbonate; In tetrachloromethane;

DOI:10.1248/cpb.40.61

Reference yield:

γ-rhodomycinone (5115-18-4,17514-35-1,31056-73-2,63640-63-1,76023-10-4,100064-16-2) → β-Rhodomycinone (5012-65-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / CH₂Cl₂ / 3 h / Ambient temperature

2: Br₂ / CCl₄ / 0.5 h / Irradiation

3: 1.) 0.1 N NaHCO₃, 2.) 0.1 N NaOH / 1.) Et₂O, 5 deg C, 15 min, 2.) Et₂O, 5 deg C, 5 min

With sodium hydroxide; bromine; sodium hydrogencarbonate; In tetrachloromethane; dichloromethane;

DOI:10.1248/cpb.40.61

upstream raw materials:

γ-Rhodomycinon

10-O-trifluoroacetyl-β-rhodomycinone

betaclamycin T

10-O-trifluoroacetyl-γ-rhodomycinone

Downstream raw materials:

γ-Rhodomycinon

10-O-(4'-p-nitrobenzoyl-3'-N-trifluoroacetyl-α-L-daunosaminyl)-β-rhodomycinone

4-Nitro-benzoic acid (2S,3S,4S,6R)-6-((1S,3R,4R)-3-ethyl-3,4,5,10,12-pentahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester

C₂₇H₂₃BO₈

Refernces

• 1、 Kita, Yasuyuki,Maeda, Hiroshi,Kirihara, Masayuki,Fujii, Yuji,Nakajima, Toyokazu,et al.. "THE FIRST TOTAL SYNTHESIS OF A POTENT β-RHODOMYCIN, OXAUNOMYCIN: REGIOSELECTIVE GLYCOSIDATION OF THE C-7 HYDROXYL GROUP OF β-RHODOMYCINONE". . p. 7173 - 7174. Retrieved 2007/10/02.
• 2、 Ihn,Schlegel,Fleck,Tresselt,Gutsche,Sedmera,Vokoun. "Anthracyclinantibiotics genetically modified streptomycetes. isolation, elucidation of structure by spectroscopical methods and biological activity of β-rhodomycin-I". . p. 176 - 180. Retrieved 2007/10/02.