2',3'-O-isopropylidene-5-pyrrolidinomethyluridine | 72470-16-7

• 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'-O-isopropylidene-5-pyrrolidinomethyluridine
• 英文别名: 1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-(pyrrolidin-1-ylmethyl)pyrimidine-2,4-dione
• CAS: 72470-16-7
• 化学式: C₁₇H₂₅N₃O₆
• 分子量: 367.402
• InChiKey: GDGUYPVWNGYEFW-RGCMKSIDSA-N

物化性质

• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2',3'-O-isopropylidene-5-pyrrolidinomethyluridine 生成 1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-[(1-methylpyrrolidin-1-ium-1-yl)methyl]pyrimidine-2,4-dione;iodide
  参考文献：
  名称：

  BADMAN, GEOFFREY T.;REESE, COLIN B., J. CHEM. SOC. CHEM. COMMUN.,(1987) N 22, 1732-1734

  摘要：

  DOI：
• 作为产物：
  描述：

  四氢吡咯 、 聚合甲醛 、 2’,3’邻异亚丙基尿苷 以 水 为溶剂， 生成 2',3'-O-isopropylidene-5-pyrrolidinomethyluridine
  参考文献：
  名称：

  2'-脱氧尿苷向胸苷的转化及相关研究

  摘要：

  通过对尿苷的5-甲基化同样有效并且对于将1- β - D-阿拉伯呋喃糖基尿嘧啶转化为其5-甲基衍生物更有效的方法，将未保护的2'-脱氧尿苷分为三个步骤转化为胸苷。

  DOI：

  10.1039/c39830000877

文献信息

• The synthesis of 5-carboxymethylaminomethyluridine and 5-carboxymethylaminomethyl-2-thiouridine
  作者：Colin B. Reese、Yogesh S. Sanghvi

  DOI：10.1039/c39840000062

  日期：——

  2′,3′-O-Isopropylideneuridine (1a) and 2′,3′-O-isopropylidene-2-thiouridine (1b) are converted in 4 steps, via the corresponding Mannich bases (2a) and (2b), into the modified nucleosides (5a) and (5b), respectively.

  2'，3'- Ô -Isopropylideneuridine（1A）和2'，3'- ö异亚丙基-2-硫代尿苷（1B）被转换以4个步骤，通过相应的曼尼期碱（2A）和（2B），进修饰的核苷（5a）和（5b）。
• Reactions between methiodides of nucleoside mannich bases and carbon nucleophiles
  作者：Geoffrey T. Badman、Colin B. Reese

  DOI：10.1039/c39870001732

  日期：——

  The conversion of the Mannich base methiodide (5) into the 5-substituted uridine derivatives [(7a), (7b), and (7c)] is described; (8) is similarly converted into the 5-substituted 1-β-D-arabinofuranosyluracil derivatives [(10a) and (10c)].

  描述了曼尼希碱甲硫醚（5）到5-取代的尿苷衍生物[（7a），（7b）和（7c）]的转化。将（8）类似地转化为5-取代的1-β- D-呋喃糖基尿嘧啶衍生物[（10a）和（10c）]。
• Chemical Synthesis and Properties of 5-Taurinomethyluridine and 5-Taurinomethyl-2-thiouridine
  作者：Toshihiko Ogata、Tomomi Shimazaki、Tadashi Umemoto、Shinya Kurata、Takashi Ohtsuki、Tsutomu Suzuki、Takeshi Wada

  DOI：10.1021/jo802697r

  日期：2009.3.20

  Unique taurine-containing Uridine derivatives, 5-taurinomethyluridine (tau m(5)U) and 5-taurinomethyl-2-thiouridine (tau m(5)s(2)U), which were discovered in mammalian mitochondrial tRNAs, exist at the first position of the anticodon. In this paper, we report the first efficient synthesis of tau m(5)U and tau m(5)s(2)U and describe their physicochemical properties. These modified ribonucleosides were synthesized by the reaction of 5-substituted uridine derivatives with a tetrabutylammonium salt of taurine that is highly reactive and well-soluble in common organic solvents. UV and H-1 NMR spectrometric studies revealed the structural properties of the taurine-containing base moieties and the Sugar conformations of these modified ribonucleosides.