O6-(allyl)-2',3',5'-tri-O-(tert-butyldimethylsilyl)inosine | 1246922-78-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: O6-(allyl)-2',3',5'-tri-O-(tert-butyldimethylsilyl)inosine
• 英文别名: [(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-(6-prop-2-enoxypurin-9-yl)oxolan-2-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 1246922-78-0
• 化学式: C₃₁H₅₈N₄O₅Si₃
• 分子量: 651.082
• InChiKey: NFXNNMWQIKBQLH-ZYWWQZICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.09
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  89.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  O⁶-(benzotriazol-1-yl)-2',3',5'-tris-O-(tert-butyldimethylsilyl)inosine 、 烯丙醇 在 caesium carbonate 作用下， 反应 0.33h， 以96 mg的产率得到O6-(allyl)-2',3',5'-tri-O-(tert-butyldimethylsilyl)inosine
  参考文献：
  名称：

  One-Pot Etherification of Purine Nucleosides and Pyrimidines

  摘要：

  A one-pot synthesis of ethers derived from inosine, guanosine, 2'-deoxyguanosine, and pyrimidinones is described Exposure of the heterocycle to 1H-benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and Cs2CO3 produces a reactive intermediate, which is converted to the desired ether by subsequent addition of an appropriate alcohol or phenol and Cs2CO3. Although rapid formation of HMPA from BOP can occur in the presence of an alcohol and base, as demonstrated by the reaction with methanol, under appropriate conditions these heteroaryl ethers can be efficiently synthesized

  DOI：

  10.1021/ol101655h

文献信息

• One-Pot Etherification of Purine Nucleosides and Pyrimidines
  作者：Hari Prasad Kokatla、Mahesh K. Lakshman

  DOI：10.1021/ol101655h

  日期：2010.10.15

  A one-pot synthesis of ethers derived from inosine, guanosine, 2'-deoxyguanosine, and pyrimidinones is described Exposure of the heterocycle to 1H-benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and Cs2CO3 produces a reactive intermediate, which is converted to the desired ether by subsequent addition of an appropriate alcohol or phenol and Cs2CO3. Although rapid formation of HMPA from BOP can occur in the presence of an alcohol and base, as demonstrated by the reaction with methanol, under appropriate conditions these heteroaryl ethers can be efficiently synthesized