29742-69-6Relevant academic research and scientific papers
Synthesis and antitumor activity of 7-O-(3,4-di-O-acetyl-2,6-dideoxy-alpha-L-lyxo-hexopyranosyl)adriamycinone.
Horton,Priebe,Turner
, p. 11 - 25 (1981)
The title compound (7), the 3'-acetoxy-4'-O-acetyl analog of adriamycin (doxorubicin), was synthesized in approximately 50% net yield from daunomycinone by bromination at C-14, glycosylation of the product at O-7 with 3,4-di-O-acetyl-2,6-dideoxy-alpha-L-l
Convenient syntheses of daunomycinone-7-D-glucuronides and doxorubicinone-7-D-glucuronides
Rho, Young S.,Kim, Sun Y.,Kim, Wan-Joong,Yeo, Keun Yun,Hong, Sig Sin,Dong, Jin Yoo
, p. 3497 - 3511 (2007/10/03)
The first synthesis of new doxorubicin and daunomycin analogs containing glucuronic acid moieties instead of daunosamine are described. The desired products, daunomycinone-7-D-glucuronide (DM7G, 10) and doxorubicinone-7-D- glucuronide (DX7G, 11) were conveniently prepared through the glycosylation at 7-hydroxyl group of daunomycinone (4) or 14-acetoxydoxorubicinone (6) with glucuronic acid derivative 7 by the Koenigs-Knorr procedure followed by alkaline deacetylatipn using aqueous LiOH solution and amberlite cation exchange material. The anomeric configuration and conformation of all products were fully characterized by assignment of 1H NMR chemical shifts and H-H coupling constants based on reported literatures.
Synthesis of 14-fluorodoxorubicin
Berettoni,Cipollone,Olivieri,Palomba,Arcamone,Maggi,Animati
, p. 2867 - 2871 (2007/10/03)
Synthesis of the novel anthracycline 14-fluorodoxorubicin is described. A key step in the synthesis is the hydrolysis of 14-bromo,14-fluoro derivative 14 with AgBF4 and DMSO, to give the geminal fluorohydrin system.
