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【结 构 式】

【药物名称】Ro-0094889, Ro-09-4889

【化学名称】2',3'-Di-O-acetyl-5'-deoxy-5-vinylcytidine

【CA登记号】216449-60-4

【 分 子 式 】C15H19N3O6

【 分 子 量 】337.33518

【开发单位】Chugai (Originator)

【药理作用】Chemical Delivery Systems, DRUG DELIVERY, Drug Delivery Systems, Inhibitors of the Degradation of Anticancer Drugs, Modulators of the Therapeutic Activity of Antineoplastic Agents, ONCOLYTIC DRUGS

合成路线1

Silylation of 5-iodocytosine (I) with hexamethyldisilazane, followed by condensation with 5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranoside (II) in the presence of stannic chloride provided 2',3'-di-O-acetyl-5'-deoxy-5-iodocytidine (III). The title vinylcytidine derivative was then obtained by displacement of the iodine atom of (III) with tri-n-butyl(vinyl)stannane (IV) using palladium catalyst and trifurylphosphine.

1 Hattori, K.; Suda, H.; Ishikawa, T.; Shimma, N.; Kohchi, Y.; Oikawa, N.; Ishitsuka, H. (F. Hoffmann-La Roche AG); 5'-Deoxy-cytidine derivs.. DE 19823484; EP 0882734; ES 2142763; FR 2763953; GB 2325931; JP 1998330395 .
2 Ishitsuka, H.; Kohchi, Y.; Shimma, N.; Oikawa, N.; Hattori, K.; Suda, H.; Ishikawa, T. (F. Hoffmann-La Roche AG); 5'-Deoxycytidine derivs.. EP 1060183; WO 9940099 .
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) 44976 4-amino-5-iodo-2(1H)-pyrimidinone; 5-Iodocytosine 1122-44-7 C4H4IN3O 详情 详情
(II) 44978 (2R,3R,4R)-4,5-bis(acetoxy)-2-methyltetrahydro-3-furanyl acetate C11H16O7 详情 详情
(III) 44977 (2R,3R,4R,5R)-4-(acetoxy)-2-[4-amino-5-iodo-2-oxo-1(2H)-pyrimidinyl]-5-methyltetrahydro-3-furanyl acetate C13H16IN3O6 详情 详情
(IV) 24920 tributyl(vinyl)stannane;Tributylvinylstannane;Vinyltributylstannane 7486-35-3 C14H30Sn 详情 详情
Extended Information