2,5-dideoxy-5-fluoro-5-methyluridine | 129802-11-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2,5-dideoxy-5-fluoro-5-methyluridine
• 英文别名: 1-[(2R,4S,5R)-5-ethyl-4-hydroxyoxolan-2-yl]-5-fluoropyrimidine-2,4-dione
• CAS: 129802-11-5
• 化学式: C₁₀H₁₃FN₂O₄
• 分子量: 244.223
• InChiKey: PFADMNKPUSCMNL-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3'-O-(tert-butyldimethylsilyl)-2',5'-dideoxy-5-fluoro-5'-methyluridine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以73%的产率得到2,5-dideoxy-5-fluoro-5-methyluridine
  参考文献：
  名称：

  Introduction of an alkyl group into the sugar portion of uracilnucleosides by the use of Gilman reagents.

  摘要：

  用Gilman试剂（R2CuLi）研究了尿嘧啶核苷糖部分的p-甲苯磺酰氧基被烷基取代的反应。对于2',3'-O-异亚丙基尿苷的5'-O-甲苯磺酸衍生物，得到了中等收率的5'-烷基化产物。与此相反，相应的2'-脱氧尿苷衍生物的反应则得到了更高收率的产物。还考察了在2'-脱氧尿苷衍生物的3'位进行类似取代反应的情况。

  DOI：

  10.1248/cpb.38.355

文献信息

• HAYAKAWA, HIROYUKI;ASHIZAWA, HIROSHI;TANAKA, HIROMICHI;MIYASAKA, TADASHI, CHEM. AND PHARM. BULL., 38,(1990) N, C. 355-360
  作者：HAYAKAWA, HIROYUKI、ASHIZAWA, HIROSHI、TANAKA, HIROMICHI、MIYASAKA, TADASHI

  DOI：——

  日期：——
• [EN] COMPOSITIONS AND METHODS FOR THE TREATMENT OF CANCER<br/>[FR] COMPOSITIONS ET MÉTHODES DE TRAITEMENT DU CANCER
  申请人：MOHAN M ALAPATI

  公开号：WO2016203352A2

  公开（公告）日：2016-12-22

  The compositions and compounds of Formula I, Formula II, Formula III, Formula IV which includes topoisomerase inhibitor molecular conjugates or its polymorphs, enantiomers, stereoisomers, solvates, and hydrates thereof. These compounds may be formulated as pharmaceutical compositions. The pharmaceutical compositions may be formulated for oral administration, delayed release or sustained release, transmucosal, syrup, intravenous, topical, parenteral administration, injection, subdermal, oral solution, rectal administration, nanoparticle, buccal administration or transdermal administration. Such compositions may be used to treatment of metastasis, neoplasms, metastatic carcinoma of the colon or rectum, metastatic breast cancer, platinum-resistant ovarian cancer, bevacizumab (avastin)-refractory high-grade glioma, non-small cell lung cancer (NSCLC), small cell lung cancer (SCLC), GI and solid tumors.
• Introduction of an alkyl group into the sugar portion of uracilnucleosides by the use of Gilman reagents.
  作者：Hiroyuki HAYAKAWA、Hiroshi ASHIZAWA、Hiromichi TANAKA、Tadashi MIYASAKA

  DOI：10.1248/cpb.38.355

  日期：——

  Substitution of a p-toluenesulfonyloxy group in the sugar portion of uracilnucleosides by an alkyl group was investigated by using Gilman reagents (R2CuLi). In the cases of 5'-O-tosyl derivatives of 2', 3'-O-isopropylideneuridine, moderate vields of 5'-alkylated products were obtained. In contrast to this, the reactions of the corresponding 2'-deoxyuridine derivatives gave higher yields of products. A similar substitution reaction at the 3'-position of 2'-deoxyuridine derivatives was also examined.

  用Gilman试剂（R2CuLi）研究了尿嘧啶核苷糖部分的p-甲苯磺酰氧基被烷基取代的反应。对于2',3'-O-异亚丙基尿苷的5'-O-甲苯磺酸衍生物，得到了中等收率的5'-烷基化产物。与此相反，相应的2'-脱氧尿苷衍生物的反应则得到了更高收率的产物。还考察了在2'-脱氧尿苷衍生物的3'位进行类似取代反应的情况。