1-((2S,3S,5S)-2,5-Bis-trityloxymethyl-tetrahydro-furan-3-yl)-4-hydroxy-1H-pyrimidin-2-one | 798574-38-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-((2S,3S,5S)-2,5-Bis-trityloxymethyl-tetrahydro-furan-3-yl)-4-hydroxy-1H-pyrimidin-2-one
• CAS: 798574-38-6
• 化学式: C₄₈H₄₂N₂O₅
• 分子量: 726.872
• InChiKey: HUDQPQKMOPCJGJ-AAVUUNPCSA-N

物化性质

• 密度：
  1.218±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.66
• 重原子数：
  55.0
• 可旋转键数：
  13.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  82.81
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-((2S,3S,5S)-2,5-Bis-trityloxymethyl-tetrahydro-furan-3-yl)-4-hydroxy-1H-pyrimidin-2-one 在 4-二甲氨基吡啶 、 2,4,6-三异丙基苯磺酰氯 、 ammonium hydroxide 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以76%的产率得到4-Amino-1-((2S,3S,5S)-2,5-bis-trityloxymethyl-tetrahydro-furan-3-yl)-1H-pyrimidin-2-one
  参考文献：
  名称：

  Ring-expanded analogues of natural oxetanocin

  摘要：

  Synthesis of ring-expanded analogs of the natural compound, oxetanocin is described. The starting material for the synthesis of the series, 4-7, was D-glucosamine and introduction of the base moiety was done through the stereochemically appropriate epoxide. For the enantiomeric series, 8-11, the starting material was D-glucose and preparation of the key intermediate involved a rearrangement reaction. The structures of the target molecules were established by NMR, HRMS, optical rotation and UV data. Single-crystal X-ray data confirmed the enantiomeric structural assignments. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.087
• 作为产物：
  描述：

  (2R,3R,4R,5R)-3,4-dihydroxy-2,5-di(trityloxymethyl)tetrahydrofuran 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 59.5h， 生成 1-((2S,3S,5S)-2,5-Bis-trityloxymethyl-tetrahydro-furan-3-yl)-4-hydroxy-1H-pyrimidin-2-one
  参考文献：
  名称：

  Ring-expanded analogues of natural oxetanocin

  摘要：

  Synthesis of ring-expanded analogs of the natural compound, oxetanocin is described. The starting material for the synthesis of the series, 4-7, was D-glucosamine and introduction of the base moiety was done through the stereochemically appropriate epoxide. For the enantiomeric series, 8-11, the starting material was D-glucose and preparation of the key intermediate involved a rearrangement reaction. The structures of the target molecules were established by NMR, HRMS, optical rotation and UV data. Single-crystal X-ray data confirmed the enantiomeric structural assignments. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.087