3',5'-di-O-benzoyl-2'-deoxycytidine | 20963-97-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3',5'-di-O-benzoyl-2'-deoxycytidine
• 英文别名: 3',5'-O-O-Dibenzoyldeoxycytidine；O^3'_,O5'-dibenzoyl-2'-deoxy-cytidine；3',5'-Di-O-benzoyl-desoxycytidin；[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-benzoyloxyoxolan-2-yl]methyl benzoate
• CAS: 20963-97-7
• 化学式: C₂₃H₂₁N₃O₆
• 分子量: 435.436
• InChiKey: ASOIJLGNYCGVKG-NLWGTHIKSA-N

物化性质

• 熔点：
  202-205 °C
• 沸点：
  614.9±65.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3',5'-di-O-benzoyl-2'-deoxycytidine 在 ammonium hydroxide 作用下， 生成 2'-脱氧胞嘧啶核苷
  参考文献：
  名称：

  Selective N-deacylation of N,O-protected nucleosides by zinc bromide

  摘要：

  DOI：

  10.1016/s0040-4039(01)82014-1
• 作为产物：
  描述：

  N⁴,O^3',O^5'-tribenzoyl-2'-deoxycytidine 在 zinc dibromide 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 16.0h， 以93.6%的产率得到3',5'-di-O-benzoyl-2'-deoxycytidine
  参考文献：
  名称：

  Selective N-deacylation of N,O-protected nucleosides by zinc bromide

  摘要：

  DOI：

  10.1016/s0040-4039(01)82014-1

文献信息

• Benzoyl Cyanide: A Mild and Efficient Reagent for Benzoylation of Nucleosides
  作者：Ashok K. Prasad、Vineet Kumar、Jyotirmoy Maity、Zhiwei Wang、Vasulinga T. Ravikumar、Yogesh S. Sanghvi、Virinder S. Parmar

  DOI：10.1081/scc-200051693

  日期：2005.4.1

  Abstract Efficient benzoylation of various nucleosides has been accomplished in pyridine with a catalytic amount of DMAP and benzoyl cyanide under mild conditions.

  摘要 在温和条件下，使用催化量的 DMAP 和苯甲酰氰在吡啶中实现了各种核苷的有效苯甲酰化。
• ‘Green’ methodology for efficient and selective benzoylation of nucleosides using benzoyl cyanide in an ionic liquid
  作者：Ashok K. Prasad、Vineet Kumar、Shashwat Malhotra、Vasulinga T. Ravikumar、Yogesh S. Sanghvi、Virinder S. Parmar

  DOI：10.1016/j.bmc.2005.04.038

  日期：2005.7

  Benzoyl cyanide in the ionic liquid 1-methoxyethyl-3-methylimidazolium methanesulfonate has been employed as a 'green' alternative and mild reaction condition protocol to conventional pyridine-benzoyl chloride system for efficient and selective benzoylation of nucleosides (of both the ribo- and deoxyribo-series) at ambient temperatures. The use of benzoyl cyanide-ionic liquid combination has been successfully

  离子液体1-甲氧基乙基-3-甲基咪唑鎓甲磺酸盐中的苯甲酰氰已被用作常规吡啶-苯甲酰氯系统的“绿色”替代方案，反应条件温和，可用于核糖（核糖和脱氧核糖两者）的有效和选择性苯甲酰化系列）。苯甲酰基氰化物-离子液体组合的使用已成功扩展到酚，芳族胺，苄醇，脂肪族二醇，3-氨基苯酚和2-氨基苄基醇的高效苯甲酰化，这表明该苯甲酰化体系的多功能性。
• MILD, EFFICIENT, SELECTIVE AND “GREEN” BENZOYLATION OF NUCLEOSIDES USING BENZOYL CYANIDE IN IONIC LIQUID
  作者：Ashok K. Prasad、Vineet Kumar、Jyotirmoy Maity、Yogesh S. Sanghvi、Vasulinga T. Ravikumar、Virinder S. Parmar

  DOI：10.1081/ncn-200060065

  日期：2005.4.1

  Use of benzoyl cyanide (BzCN) for benzoylation Of nucleasides has been studied, both in pyridine and in ionic liquid. BzCN in 1-methoxyethyl-3-methylimidazolium methanesulfonate as ionic liquid has been found to be a "green" alternative compared to the pyridine-BzCN system An efficient and selective benzoylation of nucleosides of both, the 2'-deoxy- and the ribo-series at ambient temperature was accomplished.
• A Mild and Rapid Glycosylation Reaction between Pyrimidine Bases and 2-Deoxyrobofuranosyl N,N,N',N'-Tetramethylphosphoroamidates
  作者：Shiro Ikegami、Takamasa Iimori、Hiroshi Kobayashi、Shun-ichi Hashimoto

  DOI：10.3987/com-95-s71

  日期：——