2',3'-dideoxy-2'-C-methylidene-5-methyl uridine

• 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',3'-dideoxy-2'-C-methylidene-5-methyl uridine
• 英文别名: 1-[(2R,5S)-5-(hydroxymethyl)-3-methylene-tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione；1-[(2R,5S)-5-(hydroxymethyl)-3-methylideneoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• 化学式: C₁₁H₁₄N₂O₄
• 分子量: 238.243
• InChiKey: QCFZMJMPBUYSSW-WCBMZHEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  [(2S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-4-methylideneoxolan-2-yl]methyl acetate 在 氨 作用下， 以 甲醇 为溶剂， 反应 3.5h， 以80%的产率得到2',3'-dideoxy-2'-C-methylidene-5-methyl uridine
  参考文献：
  名称：

  A new route to 2′-C-methylene nucleoside analogs, inhibitors of ribonucleotide reductase

  摘要：

  Glycosyl phenyl sulfone obtained in 4 steps from isosaccharino-lactone was convened into a 2'-C-acetoxymethylfuranoid glycal with SmI2-HMPA. Coupling of this glycal with silylated thymine or cytidine in the presence of Pd(0) led after deprotection, to the 2'-deoxy-2'-methylidene-5-methyluridine and to tire 2'-deoxy-2'-methylidene cytosine, respectively.

  DOI：

  10.1016/0040-4039(95)00550-v

文献信息

• A new route to 2′-C-methylene nucleoside analogs, inhibitors of ribonucleotide reductase
  作者：Renée Pontikis、Junior Wolf、Claude Monneret、Jean-Claude Florent

  DOI：10.1016/0040-4039(95)00550-v

  日期：1995.5

  Glycosyl phenyl sulfone obtained in 4 steps from isosaccharino-lactone was convened into a 2'-C-acetoxymethylfuranoid glycal with SmI2-HMPA. Coupling of this glycal with silylated thymine or cytidine in the presence of Pd(0) led after deprotection, to the 2'-deoxy-2'-methylidene-5-methyluridine and to tire 2'-deoxy-2'-methylidene cytosine, respectively.