1-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-β-D-ribofuranosyl]uracil | 1050244-54-6

• 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: 1-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-β-D-ribofuranosyl]uracil
• 英文别名: [(6aR,8R,9R,9aS)-8-(2,4-dioxopyrimidin-1-yl)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-selenopheno[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl] 2,4-dimethoxybenzoate
• CAS: 1050244-54-6
• 化学式: C₃₀H₄₆N₂O₉SeSi₂
• 分子量: 713.834
• InChiKey: DPTVKIFVSFCUFN-YULOIDQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-β-D-ribofuranosyl]uracil 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (2R,3R,4S,5R)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydroselenophen-3-yl 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
• 作为产物：
  描述：

  1,4-anhydro-4-seleno-D-ribitol 在 吡啶 、 2,6-二甲基吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 生成 1-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-seleno-β-D-ribofuranosyl]uracil
  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

文献信息

• Practical synthesis of 4′-selenopyrimidine nucleosides using hypervalent iodine
  作者：Hirotsugu Taniike、Yusuke Inagaki、Akira Matsuda、Noriaki Minakawa

  DOI：10.1016/j.tet.2011.08.020

  日期：2011.10

  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.