1,4-anhydro-4-seleno-D-ribitol | 1080622-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-anhydro-4-seleno-D-ribitol
• CAS: 1080622-02-1
• 化学式: C₅H₁₀O₃Se
• 分子量: 197.093
• InChiKey: MFVCMPDBWIMAQY-LMVFSUKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.37
• 重原子数：
  9.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.69
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  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 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 24.25h， 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-2,3,5-tri-O-(p-methoxybenzyl)-4-seleno-D-ribitol 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到1,4-anhydro-4-seleno-D-ribitol
  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