IDN-5390

Chemical Name: 2-O-Acetyl-1,3-anhydro-2-C-[(1S,2S,3R,9S)-2-(benzoyloxy)-9-[3(S)-(tert-butoxycarboxamido)-2(R)-hydroxy-5-methylhexanoyloxy]-1,5-dihydroxy-4,8,11,11-tetramethyl-6-oxobicyclo[5.3.1]undeca-4,7-dien-3-yl]-4-deoxy-D-erythro-pentitol; Benzoic acid (1S,2S,3R,9S)-3-[(2R,3S)-3-(acetoxy)-2-(2-hydroxyethyl)-3-oxetanyl]-9-[(2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-5-methylhexanoyloxy]-1,5-dihydroxy-4,8,11,11-tetramethyl-6-oxobicyclo[5.3.1]undeca-4,7-dien-2-yl ester
CAS No. 191276-31-0
项目整合开发状态: Preclinical
项目研究机构: Indena (Originator), Ist. di Ricerche Farmacol. Mario Negri (Codevelopment)
合成路线:Oxidation of 10-deacetylbaccatin III (I) by means of cupric acetate yielded diketone (II),in equilibrium with the retroaldol product (III).Subsequent reduction employing NaBH4 and CeCl3 produced the seco-taxane (IV) as the major reaction product.Selective protection of the 7 and 9 hydroxyl groups was achieved by treatment with chlorotriethylsilane and imidazole.The resultant 7,9-disilylated derivative (V) was then acylated by the oxazolidinecarboxylic acid (VI) to furnish,after acidic hydrolysis,the title C-seco taxane derivative.