5'-O-tert-butyldimethylsilylthymidine-3'-O-1,3,2-oxathiaphospholane | 400019-99-0

• 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: 5'-O-tert-butyldimethylsilylthymidine-3'-O-1,3,2-oxathiaphospholane
• CAS: 400019-99-0
• 化学式: C₁₈H₃₁N₂O₆PSSi
• 分子量: 462.579
• InChiKey: MSUGFDIFPIHPBG-WCRROROBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  91.78
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5'-O-tert-butyldimethylsilylthymidine-3'-O-1,3,2-oxathiaphospholane 在 borane-N,N-diisopropylethylamine complex 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  THE SYNTHESIS OF DITHYMIDINE BORANOPHOSPHATE BY THE OXATHIAPHOSPHOLANE APPROACH

  摘要：

  The application of the oxathiaphospholane approach for the synthesis of dithymidine boranphospate was evaluated. It was shown, that although the nucleoside-3'-O-oxathiaphospholane-borane complexes 2 or 6 could not be chromatographically separated into diastereomerically pure species due to their apparent instability to moisture, they can be successfully applied to the non-stereocontrolled formation of internucleotide boranophosphate bond by reaction with 5'-OH-nucleoside in the presence of DBU. Attempts to apply the related dithiaphospholane approach for the preparation of dithymidine boranophosphorothioate were unsuccessful.

  DOI：

  10.1081/ncn-100107195
• 作为产物：
  描述：

  5’-O-(叔丁基二甲基甲硅烷基)胸苷 、 2-N,N-diisopropylamino-1,3,2-oxathiaphospholane 在 四氮唑 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到5'-O-tert-butyldimethylsilylthymidine-3'-O-1,3,2-oxathiaphospholane
  参考文献：
  名称：

  THE SYNTHESIS OF DITHYMIDINE BORANOPHOSPHATE BY THE OXATHIAPHOSPHOLANE APPROACH

  摘要：

  The application of the oxathiaphospholane approach for the synthesis of dithymidine boranphospate was evaluated. It was shown, that although the nucleoside-3'-O-oxathiaphospholane-borane complexes 2 or 6 could not be chromatographically separated into diastereomerically pure species due to their apparent instability to moisture, they can be successfully applied to the non-stereocontrolled formation of internucleotide boranophosphate bond by reaction with 5'-OH-nucleoside in the presence of DBU. Attempts to apply the related dithiaphospholane approach for the preparation of dithymidine boranophosphorothioate were unsuccessful.

  DOI：

  10.1081/ncn-100107195