Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-5-(2-thioxo-2λ⁵-[1,3,2]oxathiaphospholan-2-yloxymethyl)-tetrahydro-furan-3-yl ester | 857447-46-2

• 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: Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-5-(2-thioxo-2λ⁵-[1,3,2]oxathiaphospholan-2-yloxymethyl)-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3R,4R,5R)-5-(4-acetamido-2-oxopyrimidin-1-yl)-4-acetyloxy-2-[(2-sulfanylidene-1,3,2lambda5-oxathiaphospholan-2-yl)oxymethyl]oxolan-3-yl] acetate；[(2R,3R,4R,5R)-5-(4-acetamido-2-oxopyrimidin-1-yl)-4-acetyloxy-2-[(2-sulfanylidene-1,3,2λ5-oxathiaphospholan-2-yl)oxymethyl]oxolan-3-yl] acetate
• CAS: 857447-46-2
• 化学式: C₁₇H₂₂N₃O₉PS₂
• 分子量: 507.482
• InChiKey: WRTUOJYEDYJWPH-FDTCPXPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  199
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-5-(2-thioxo-2λ⁵-[1,3,2]oxathiaphospholan-2-yloxymethyl)-tetrahydro-furan-3-yl ester 在 氨 、 tris(tetra-n-butylammonium) hydrogen pyrophosphate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 alpha-thio-CTP
  参考文献：
  名称：

  Synthesis of Nucleoside α-Thiotriphosphates via an Oxathiaphospholane Approach^†

  摘要：

  Nucleoside 5 '-O-(alpha-thiotriphosphates) were obtained in reactions of the appropriate nucleoside 5 '-O-(2-thio-1,3,2-oxathiaphospholanes) with pyrophosphate in the presence of DBU. The presented method allows also for preparation of alpha-seleno congeners and corresponding a-modified diphosphates.

  DOI：

  10.1021/ol050617r
• 作为产物：
  描述：

  2-氯-1,3,2-氧杂硫杂磷杂环戊烷 、 N-acetyl-2',3'-di-O-acetylcytidine 在 吡啶 、 sulfur 作用下， 反应 16.0h， 以78%的产率得到Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-5-(2-thioxo-2λ⁵-[1,3,2]oxathiaphospholan-2-yloxymethyl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Synthesis of Nucleoside α-Thiotriphosphates via an Oxathiaphospholane Approach^†

  摘要：

  Nucleoside 5 '-O-(alpha-thiotriphosphates) were obtained in reactions of the appropriate nucleoside 5 '-O-(2-thio-1,3,2-oxathiaphospholanes) with pyrophosphate in the presence of DBU. The presented method allows also for preparation of alpha-seleno congeners and corresponding a-modified diphosphates.

  DOI：

  10.1021/ol050617r