NSC-639830, IST-622, -Drug Synthesis Database

【结构式】

【药物名称】NSC-639830, IST-622

【化学名称】6-O-Ethoxypropionyl-3',4'-O-(exo-benzylidene)chartreusin
　　　　　　10-[3,4-O-exo-Benzylidene-2-O-(alpha-D-digitalosyl)-beta-D-fucosyloxy]-6-(3-ethoxypropionyloxy)-1-methyl-5,12-dihydrobenzo[h][1]benzopyrano[5,4,3-cde][1]benzopyran-5,12-dione
　　　　　　10-[3,4-O-exo-Benzylidene-6-deoxy-2-O-(6-deoxy-3-O-methyl-alpha-D-galactopyranosyl)-beta-D-galactopyranosyloxy]-6-(3-ethoxypropionyloxy)-1-methyl-5,12-dihydrobenzo[h][1]benzopyrano[5,4,3-cde][1]benzopyrano-5,12-dione

【CA登记号】128201-92-3

【分子式】C₄₄H₄₄O₁₆

【分子量】828.83168

【开发单位】Ishihara Sangyo (Originator), Mitsui Pharmaceuticals (Codevelopment)

【药理作用】Antibiotics and Alkaloids, Antineoplastic Antibiotics, ONCOLYTIC DRUGS

合成路线1

Ketalization of chartreusin (I) with benzaldehyde (II) using p-toluenesulfonic acid in the presence of molecular sieves, yielded the corresponding 3',4'-O-benzylidene derivative as a mixture of endo- and exo-isomers, which were separated by column chromatography. The required exo-isomer (III) was then esterified with 3-ethoxypropionic acid (IV) by means of DCC, producing the title ester.

参考文献中间体

【1】 Kon, K.; et al.; Synthesis and cytostatic activity of the antitumor antibiotic chartreusin derivatives. J Antibiot 1990, 43, 4, 372.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	59134	10-[((2S,3R,4S,5R,6R)-3-{[(2R,3R,4S,5R,6R)-3,5-dihydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy]-6-hydroxy-1-methylbenzo[h]chromeno[5,4,3-cde]chromene-5,12-dione		C₃₂H₃₂O₁₄	详情	详情
(II)	10498	Benzaldehyde;Benzoic aldehyde;Phenylmethanal	100-52-7	C₇H₆O	详情	详情
(III)	59135	10-[((2S,3aR,4R,6S,7R,7aS)-7-{[(2R,3R,4S,5R,6R)-3,5-dihydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-4-methyl-2-phenyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)oxy]-6-hydroxy-1-methylbenzo[h]chromeno[5,4,3-cde]chromene-5,12-dione		C₃₉H₃₆O₁₄	详情	详情
(IV)	59136	3-Ethoxypropionic acid; o-Ethoxypropionic acid	4324-38-3	C₅H₁₀O₃	详情	详情

Extended Information