[hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphinothioyl] dihydrogen phosphate | 81811-21-4

• 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: [hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphinothioyl] dihydrogen phosphate
• CAS: 81811-21-4
• 化学式: C₁₀H₁₆N₂O₁₀P₂S
• 分子量: 418.258
• InChiKey: QHZCCYRQFJPFEO-ZWPOATFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.16
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  180.54
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  在 氨 作用下， 以 乙腈 为溶剂， 生成 [hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphinothioyl] dihydrogen phosphate
  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

文献信息

• Diastereomerically pure nucleoside-5′-O-(2-thio-4,4-pentamethylene-1,3,2-oxathiaphospholane)s-Substrates for synthesis of P-chiral derivatives of nucleoside-5′-O-phosphorothioates
  作者：Agnieszka Tomaszewska、Piotr Guga、Wojciech J. Stec

  DOI：10.1002/chir.20905

  日期：2011.3

  A method for stereocontrolled chemical synthesis of P‐substituted nucleoside 5′‐O‐phosphorothioates has been elaborated. Selected 3′‐O‐acylated deoxyribonucleoside‐ and 2′,3′‐O,O‐diacylated ribonucleoside‐5′‐O‐(2‐thio‐4,4‐pentamethylene‐1,3,2‐oxathiaphospholane)s were chromatographically separated into P‐diastereomers. Their reaction with anions of phosphorus‐containing acids was highly stereoselective

  拟定了一种立体控制化学合成P-取代核苷5'- O-硫代磷酸酯的方法。选择3' ø -acylated deoxyribonucleoside-和2'，3'- O，O- -diacylated核糖核苷-5'- Ö - （2-硫代-4,4-五亚甲基-1,3,2-oxathiaphospholane）类是色谱法分为P-非对映异构体。它们与含磷酸阴离子的反应具有很高的立体选择性（≥90％），并以令人满意的产率提供了相应的P-手性α-硫代二磷酸及其膦酸酯类似物。手性，2011年。©2010 Wiley-Liss，Inc.。
• LUDWIG, JANOS;ECKSTEIN, FRITZ, J. ORG. CHEM., 54,(1989) N, C. 631-635
  作者：LUDWIG, JANOS、ECKSTEIN, FRITZ

  DOI：——

  日期：——