sodium;N-[(2R,3R,4R,5S,6R)-2-[[(2R,3R,4S,5R,6R)-6-[(2S,3S,4R,5R,6R)-2-carboxy-4,5-dihydroxy-6-[[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(4-methoxyphenoxy)oxan-2-yl]methoxy]oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]ethanimidate | 1340473-50-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: sodium;N-[(2R,3R,4R,5S,6R)-2-[[(2R,3R,4S,5R,6R)-6-[(2S,3S,4R,5R,6R)-2-carboxy-4,5-dihydroxy-6-[[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(4-methoxyphenoxy)oxan-2-yl]methoxy]oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]ethanimidate
• CAS: 1340473-50-8
• 化学式: C₃₉H₅₈NO₂₈*Na
• 分子量: 1011.87
• InChiKey: NGQXUNPVIQWYJJ-IIHYSSCZSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -12.95
• 重原子数：
  69
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  458
• 氢给体数：
  15
• 氢受体数：
  29

反应信息

• 作为产物：
  描述：

  在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 20 % Pd(OH)2/C 、 氢气 作用下， 以 四氢呋喃 、 水 、 叔丁醇 、 甲醇 为溶剂， 反应 27.0h， 以350 mg的产率得到sodium;N-[(2R,3R,4R,5S,6R)-2-[[(2R,3R,4S,5R,6R)-6-[(2S,3S,4R,5R,6R)-2-carboxy-4,5-dihydroxy-6-[[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(4-methoxyphenoxy)oxan-2-yl]methoxy]oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]ethanimidate
  参考文献：
  名称：

  Convergent synthesis of the pentasaccharide repeating unit of the O-antigen of Shigella boydii type 14

  摘要：

  An efficient synthesis of the pentasaccharide repeating unit of the O-antigen of Shigella boydii type 14 is reported. A one-pot, two step iterative glycosylation and [3+2] block synthetic strategy have been adopted for the construction of the pentasaccharide derivative 11, which was then transformed into target compound 1 after a series of functional group transformations. The primary hydroxyl group has been selectively oxidized to a carboxylic acid functionality without affecting the secondary hydroxyl groups. HClO4-SiO2 has been used as a solid acid substitute in all glycosylation and functional group transformations. The yields were excellent in all glycosylation steps. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.004