(1R,1'R)-((6S,6'S,7R,7'R)-diselanediylbis(2,2,4,4-tetraisopropyl-1,3,5,2,4-trioxadisilocane-7,6-diyl))bis(2-oxoethane-1,1-diyl) bis(2,4-dimethoxybenzoate) | 1337982-98-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,1'R)-((6S,6'S,7R,7'R)-diselanediylbis(2,2,4,4-tetraisopropyl-1,3,5,2,4-trioxadisilocane-7,6-diyl))bis(2-oxoethane-1,1-diyl) bis(2,4-dimethoxybenzoate)
• CAS: 1337982-98-5
• 化学式: C₅₂H₈₆O₁₆Se₂Si₄
• 分子量: 1237.51
• InChiKey: NTHLOZKGPVQGER-CBOOYFJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.68
• 重原子数：
  74.0
• 可旋转键数：
  23.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  179.04
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为产物：
  描述：

  1,4-anhydro-2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-D-ribitol 在 2,6-二甲基吡啶 、 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 (1R,1'R)-((6S,6'S,7R,7'R)-diselanediylbis(2,2,4,4-tetraisopropyl-1,3,5,2,4-trioxadisilocane-7,6-diyl))bis(2-oxoethane-1,1-diyl) bis(2,4-dimethoxybenzoate)
  参考文献：
  名称：

  Practical synthesis of 4′-selenopyrimidine nucleosides using hypervalent iodine

  摘要：

  We report herein a synthesis of 4'-selenouridine 12 and 4'-selenocytidine 14, substrates for the synthesis of 4'-selenoRNA. The Pummerer-like reaction between the selenoxide 9 and a silylated uracil afforded the desired 4'-selenouridine derivative 10: however, the chemical yield of 10 was rather low. In addition, the reproducibility of this reaction was poor because of the instability of the selenoxide 9. Improvement of this Pummerer-like reaction to give 10 was achieved when the 4-selenosugar 8 was treated with TMSOTf, 2,6-lutidine and the silylated uracil in the presence of iodosylbenzene. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.020