3'-O-acetylthymidine 5'-O-(2-thio-1,3,2-oxathiaphospholane) | 193093-34-4

• 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: 3'-O-acetylthymidine 5'-O-(2-thio-1,3,2-oxathiaphospholane)
• 英文别名: [(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-[(2-sulfanylidene-1,3,2lambda5-oxathiaphospholan-2-yl)oxymethyl]oxolan-3-yl] acetate；[(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-[(2-sulfanylidene-1,3,2λ5-oxathiaphospholan-2-yl)oxymethyl]oxolan-3-yl] acetate
• CAS: 193093-34-4
• 化学式: C₁₄H₁₉N₂O₇PS₂
• 分子量: 422.42
• InChiKey: XPXUHLGHCKOTSA-JPOJUUCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3'-O-acetylthymidine 5'-O-(2-thio-1,3,2-oxathiaphospholane) 在 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 2.0h， 以58%的产率得到[[[(2R,3S,5R)-3-acetyloxy-5-(5-methyl-4-oxido-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxy-sulfidophosphaniumyl]oxy-oxidophosphoryl] 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
• 作为产物：
  描述：

  2-氯-1,3,2-氧杂硫杂磷杂环戊烷 、 3'-O-acetylthymidine 在 吡啶 、 sulfur 作用下， 反应 16.0h， 以80%的产率得到3'-O-acetylthymidine 5'-O-(2-thio-1,3,2-oxathiaphospholane)
  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

• Thiophosphorylation of Biologically Relevant Alcohols by the Oxathiaphospholane Approach
  作者：Magdalena Olesiak、Danuta Krajewska、Ewa Wasilewska、Dariusz Korczyński、Janina Baraniak、Andrzej Okruszek、Wojciech J. Stec

  DOI：10.1055/s-2002-31913

  日期：——

  2-Alkoxy-2-thiono-1,3,2-oxathiaphospholanes are readily transformed into phosphorothioate monoesters of the corresponding alcohols in a one-pot process, involving the reaction with 3-hydroxypropionitrile in the presence of DBU, followed by treatment with aqueous ammonia. In this way a series of nucleoside-3′-O- and 5′-O-phosphorothioates were prepared, as well as phosphorothioate derivatives of selected polyols.

  2-烷氧基-2-硫代-1,3,2-氧硫磷烷可以方便地通过一步法转化为相应醇的磷酸硫代单酯，该方法涉及在DBU存在下与3-羟基丙腈反应，随后用氨水处理。通过这种方法制备了一系列核苷-3′-O-和5′-O-磷酸硫代酯，以及选定多元醇的磷酸硫代衍生物。
• DBU-assisted 1,3,2-oxathiaphospholane ring-opening condensation with selected O-, S-, N- and C-nucleophiles
  作者：Konrad Misiura、Daria Szymanowicz、Magdalena Olesiak、Wojciech J. Stec

  DOI：10.1016/j.tetlet.2004.04.012

  日期：2004.5

  The reactivity of protected thymidine 3'-O- and 5'-O-(2-thio-1,3,2-oxathiaphospholanes) towards various nucleophiles in the presence of DBU is presented and mechanistic implications are discussed. (C) 2004 Elsevier Ltd. All rights reserved.