TMS(-2)[TMS(-3)][TMS(-5)]D-Araf(b)-cytosin-1-yl | 51432-43-0

• 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: TMS(-2)[TMS(-3)][TMS(-5)]D-Araf(b)-cytosin-1-yl
• 英文别名: 4-amino-1-[(2R,3S,4R,5R)-3,4-bis(trimethylsilyloxy)-5-(trimethylsilyloxymethyl)oxolan-2-yl]pyrimidin-2-one
• CAS: 51432-43-0
• 化学式: C₁₈H₃₇N₃O₅Si₃
• 分子量: 459.765
• InChiKey: NATBOBHUVCMNTD-MXASKKJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  95.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  TMS(-2)[TMS(-3)][TMS(-5)]D-Araf(b)-cytosin-1-yl 在 吡啶 、 ammonium hydroxide 作用下， 反应 4.25h， 生成 1-(β-D-arabinofuranosyl)-N⁴-benzoylcytosine
  参考文献：
  名称：

  An Improved Transient Method for the Synthesis ofN-Benzoylated Nucleosides

  摘要：

  The Jones' transient method for the synthesis of N-benzoylated nucleosides is improved by reducing the amounts of chlorotrimethylsilane (TMSCI) and benzoyl chloride to nearly equivalent quantities. The easy work-up and high yields of products are the major advantages of this approach. Jones' method is further simplified by omitting the addition of ammonium hydroxide. The utility of this modification for the preparation of some useful protected nucleosides is also presented.

  DOI：

  10.1081/scc-120017200
• 作为产物：
  描述：

  三甲基氯硅烷 、 盐酸阿糖胞苷 在 吡啶 作用下， 反应 1.0h， 生成 TMS(-2)[TMS(-3)][TMS(-5)]D-Araf(b)-cytosin-1-yl
  参考文献：
  名称：

  An Improved Transient Method for the Synthesis ofN-Benzoylated Nucleosides

  摘要：

  The Jones' transient method for the synthesis of N-benzoylated nucleosides is improved by reducing the amounts of chlorotrimethylsilane (TMSCI) and benzoyl chloride to nearly equivalent quantities. The easy work-up and high yields of products are the major advantages of this approach. Jones' method is further simplified by omitting the addition of ammonium hydroxide. The utility of this modification for the preparation of some useful protected nucleosides is also presented.

  DOI：

  10.1081/scc-120017200

文献信息

• Application of the phosphoramidite-phosphite triester approach for the synthesis of combinations between oxygenated sterols and nucleoside analogues linked by phosphodiester bonds
  作者：Yu-hua Jl、Willi Bannwarth、Bang Luu

  DOI：10.1016/s0040-4020(01)85432-6

  日期：1990.1

  synthesis seems to be the technique of choice for the preparation of labile multifunctional compounds linked by phosphodiester bonds in solution. Thus, to make the lipophilic oxysterols water-soluble for biological studies, we have prepared several combinations between polyoxygenated sterols and nucleoside analogues using Cβ-cyanoethoxy)bis(diisopropylamine) phosphine 2 as phosphorylating agent. This approach

  用于固相DNA合成的最近开发的亚磷酰胺-亚磷酸三酯方法似乎是制备通过溶液中的磷酸二酯键连接的不稳定多功能化合物的选择技术。因此，为了使亲脂性氧固醇水溶性以用于生物学研究，我们使用Cβ-氰基乙氧基）双（二异丙胺）膦2作为磷酸化剂，制备了多氧固醇和核苷类似物之间的几种组合。这种方法在非常温和的条件下以相当高的收率（> 60％）提供了所需的1型化合物。
• Fadl; Hasegawa; Youssef, Pharmazie, 1995, vol. 50, # 6, p. 382 - 387
  作者：Fadl、Hasegawa、Youssef、Farag、Omar、Kawaguchi

  DOI：——

  日期：——
• JI, YU-HUA;BANNWARTH, WILLI;LUU, BANG, TETRAHEDRON, 46,(1990) N, C. 487-502
  作者：JI, YU-HUA、BANNWARTH, WILLI、LUU, BANG

  DOI：——

  日期：——
• An Improved Transient Method for the Synthesis of<i>N</i>-Benzoylated Nucleosides
  作者：Xue-Feng Zhu、Howard J. Williams、A. Ian Scott

  DOI：10.1081/scc-120017200

  日期：2003.1.5

  The Jones' transient method for the synthesis of N-benzoylated nucleosides is improved by reducing the amounts of chlorotrimethylsilane (TMSCI) and benzoyl chloride to nearly equivalent quantities. The easy work-up and high yields of products are the major advantages of this approach. Jones' method is further simplified by omitting the addition of ammonium hydroxide. The utility of this modification for the preparation of some useful protected nucleosides is also presented.