ChemicalBook CAS DataBase List (7S,9S)-9-Acetyl-9-amino-7,8,9,10-tetrahydro-6,7,11-trihydroxy-5,12-naphthacenedione

(7S,9S)-9-Acetyl-9-amino-7,8,9,10-tetrahydro-6,7,11-trihydroxy-5,12-naphthacenedione synthesis

9synthesis methods

Product Name:(7S,9S)-9-Acetyl-9-amino-7,8,9,10-tetrahydro-6,7,11-trihydroxy-5,12-naphthacenedione
CAS Number:92395-41-0
Molecular formula:C20H17NO6
Molecular Weight:367.35

A mixture of R-9-acetamido-9- [1,1- (2,2-dimethylpropanedioxy) ethyl] -4,5-dihydro-6,13-dihydroxy -4,14- Methyl-14H-anthraceno [3,2-f] - [1,3] oxazolene-7,12-dione (Compound 4, R = CH3), 1200 g of 3N sulfuric acid aqueous solution and incubated at 60-70 ° C for 8 hours. The pH of the solution was adjusted to 7-8 with aqueous sodium hydrogencarbonate solution, The combined chloroform layers were washed with water, dried, filtered and concentrated. The residue was stirred with isopropyl ether to give (+) - 9-amino-4-demethoxy-9-deoxo daunomycinone.

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(7S,9S)-9-Acetyl-9-amino-7,8,9,10-tetrahydro-6,7,11-trihydroxy-5,12-naphthacenedione

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Yield:-

Steps:

Multi-step reaction with 11 steps
1: 98.7 percent / ammonium carbonate / ethanol; H₂O / 1 h / Heating
2: 92 percent / barium hydroxide octahydrate / H₂O / 36 h / Heating
3: 94.9 percent / HCl (g) / 24 h / 25 °C
5: 1.) sodium hydride / 1.) THF, 65 deg C, 1.5 h, 2.) THF, 5 deg C - 10 deg C, 1 h
6: aq. sodium hydroxide, zinc / toluene / 2 h / 65 °C
7: pyridine / 1.) 20 deg C, 1 h, 2.) 70 deg C, 30 min
8: 90 percent / sodium chloride, aluminum chloride / 0.07 h / 170 °C
9: 88 percent / p-toluenesulfonic acid / toluene / 4 h / Heating
10: 88.5 percent / 1,3-dibromo-5,5-dimethylhydantoin / benzene / 0.25 h / Heating; Irradiation
11: 81.8 percent / 3 N aq. H₂SO₄ / 30 h / 80 °C

References:

Ishizumi, Kikuo;Ohashi, Naohito;Tanno, Norihiko [Journal of Organic Chemistry,1987,vol. 52,# 20,p. 4477 - 4485]

Acetamide, N-[(2R)-2-acetyl-1,2,3,4,6,11-hexahydro-5,12-dihydroxy-6,11-dioxo-2-naphthacenyl]-

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References

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References

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References

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References