[(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 2,2,2-trifluoroethanesulfonate | 220792-20-1

• 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: [(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 2,2,2-trifluoroethanesulfonate
• CAS: 220792-20-1
• 化学式: C₁₈H₂₉F₃N₂O₇SSi
• 分子量: 502.584
• InChiKey: YMQDKBKFTABHQN-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 2,2,2-trifluoroethanesulfonate 在 tetrabutylammonium selenocyanate 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以68%的产率得到5'-O-(t-butyldimethylsilyl)-2,3'-anhydro-1-(2'-deoxy-β-D-threo-pentofuranosyl)thymine
  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 、 5’-O-(叔丁基二甲基甲硅烷基)胸苷 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 [(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 2,2,2-trifluoroethanesulfonate
  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