1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-4-ethoxy-1H-pyrimidin-2-one | 661463-96-3

• 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: 1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-4-ethoxy-1H-pyrimidin-2-one
• 英文别名: 1-[(3aR,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-4-ethoxypyrimidin-2-one
• CAS: 661463-96-3
• 化学式: C₂₀H₃₄N₂O₆Si
• 分子量: 426.585
• InChiKey: DIYLSNFEESBURD-MWQQHZPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  78.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-4-ethoxy-1H-pyrimidin-2-one 在 lithium hexamethyldisilazane 、 氘代甲醇 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Lithiation at the 6-Position of Uridine with Lithium Hexamethyldisilazide:  Crucial Role of Temporary Silylation

  摘要：

  Lithium hexamethyldisilazide (LiHMDS) can mediate silylation at the 6-position of uridine, although LiHMDS alone is not able to generate the C-6-lithiated uridine. Experimental results showed that temporary silylation of 0-4 (or N-3) of the uracil ring triggers the C-6 lithiation with LiHMDS. This finding allowed us to develop an efficient intramolecular alkylation of 5'-deoxy-5'-iodouridine to furnish 6,5'-C-cyclouridine.

  DOI：

  10.1021/ol049500d
• 作为产物：
  描述：

  乙醇 、 5'-O-(t-butyldimethylsilyl)-2',3'-O-isopropylideneuridine 在 N-甲基吗啉 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 以51%的产率得到1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-4-ethoxy-1H-pyrimidin-2-one
  参考文献：
  名称：

  Lithiation at the 6-Position of Uridine with Lithium Hexamethyldisilazide:  Crucial Role of Temporary Silylation

  摘要：

  Lithium hexamethyldisilazide (LiHMDS) can mediate silylation at the 6-position of uridine, although LiHMDS alone is not able to generate the C-6-lithiated uridine. Experimental results showed that temporary silylation of 0-4 (or N-3) of the uracil ring triggers the C-6 lithiation with LiHMDS. This finding allowed us to develop an efficient intramolecular alkylation of 5'-deoxy-5'-iodouridine to furnish 6,5'-C-cyclouridine.

  DOI：

  10.1021/ol049500d

文献信息

• Lithiation at the 6-Position of Uridine with Lithium Hexamethyldisilazide:  Crucial Role of Temporary Silylation
  作者：Yuichi Yoshimura、Hiroki Kumamoto、Ayuka Baba、Shingo Takeda、Hiromichi Tanaka

  DOI：10.1021/ol049500d

  日期：2004.5.1

  Lithium hexamethyldisilazide (LiHMDS) can mediate silylation at the 6-position of uridine, although LiHMDS alone is not able to generate the C-6-lithiated uridine. Experimental results showed that temporary silylation of 0-4 (or N-3) of the uracil ring triggers the C-6 lithiation with LiHMDS. This finding allowed us to develop an efficient intramolecular alkylation of 5'-deoxy-5'-iodouridine to furnish 6,5'-C-cyclouridine.