2,2,2-Trifluoro-ethanesulfonic acid (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester | 220792-04-1

• 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: 2,2,2-Trifluoro-ethanesulfonic acid (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
• 英文别名: [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 2,2,2-trifluoroethanesulfonate
• CAS: 220792-04-1
• 化学式: C₁₂H₁₅F₃N₂O₇S
• 分子量: 388.322
• InChiKey: MKHJVCQOXGWKPO-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  potassium selenocyanate 、 2,2,2-Trifluoro-ethanesulfonic acid (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 以 N,N-二甲基甲酰胺 为溶剂， 反应 45.0h， 以25%的产率得到5'-deoxythymidine-5'-selenocyanate
  参考文献：
  名称：

  New nucleoside heteroanalogues: Desoxynucleoside selenocyanates

  摘要：

  Naw nucleoside heteroanalogues, 5'- and 9'-desoxynucleoside selenocyanates and primary desoxysugar selenocyanates, were synthesized from activated nucleoside and sugar derivatives and a new convenient seleno nucleophile, tetrabutylammonium selenocyanate. Tresylate-based activation of hydroxy functions turned out to be most successful for formation of these selenocyanates compared with mesylate- or triflate-based activation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02559-3
• 作为产物：
  描述：

  2,2,2-三氟乙基磺酰氯 、 beta-胸苷 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 2,2,2-Trifluoro-ethanesulfonic acid (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  New nucleoside heteroanalogues: Desoxynucleoside selenocyanates

  摘要：

  Naw nucleoside heteroanalogues, 5'- and 9'-desoxynucleoside selenocyanates and primary desoxysugar selenocyanates, were synthesized from activated nucleoside and sugar derivatives and a new convenient seleno nucleophile, tetrabutylammonium selenocyanate. Tresylate-based activation of hydroxy functions turned out to be most successful for formation of these selenocyanates compared with mesylate- or triflate-based activation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02559-3