5-iodo-2',3',5'-(triOTMS)uridine | 136368-45-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-iodo-2',3',5'-(triOTMS)uridine
• 英文别名: 1-[(2R,3R,4R,5R)-3,4-bis(trimethylsilyloxy)-5-(trimethylsilyloxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione
• CAS: 136368-45-1
• 化学式: C₁₈H₃₅IN₂O₆Si₃
• 分子量: 586.647
• InChiKey: ZJFVWAJHSPFVDS-KCYZZUKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  86.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  三甲基氯硅烷 、 5-碘尿苷 在 吡啶 、 六甲基二硅氮烷 作用下， 反应 10.0h， 以99%的产率得到5-iodo-2',3',5'-(triOTMS)uridine
  参考文献：
  名称：

  Synthèe, caractérisation et propriétés cytotoxiques des premiers ‘métallocénonucléosides’

  摘要：

  The synthesis of the first 'metallocenonucleosides' (nucleosides containing a metallocenic moiety in their framework) of the formula Ns-C = C-Fc, Ns-CH = CH-Fc and Ns-CH2-CH2-Fc (Ns = uridine, deoxyuridine, adenosine; Fc: C5H4FeC5H5) has been conducted in the presence of palladium salt according to the following routes: i) reaction of a 5-chloromercuri-nucleoside on ethynylferrocene; ii) hydrozirconation (Schwartz' reagent) of ethynylferrocene followed by the reaction of a 5-halogeno nucleoside; iii) direct coupling between ethynylferrocene and a 5-halogeno nucleoside. The same procedures allowed the synthesis of the corresponding 'metallocenonucleobases' Nb-C = C-Fc, Nb-CH = CH-Fc and NbCH2CH2Fc (Nb = uracil, cytosine, adenine) which have also been prepared by acid solvolysis of the nucleosides precursors. The compounds obtained were purified by HPLC technique and were characterized by H-1 NMR and mass spectrometry. The cytotoxicity in vitro has been studied on L 1210 cells. Only modest activity has been observed.

  DOI：

  10.1016/0223-5234(91)90070-4