(S)-3-(4-hydroxyphenyl)-2-(carbobenzyloxyamino)-N-((1R,2S,3R,5S,6S,9R,10S)-1,2,9,10-tetrahydroxy-5-(carbobenzyloxyamino)-7-oxaspiro[5.6]dodecan-3-yl)propanamide | 1569043-59-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-3-(4-hydroxyphenyl)-2-(carbobenzyloxyamino)-N-((1R,2S,3R,5S,6S,9R,10S)-1,2,9,10-tetrahydroxy-5-(carbobenzyloxyamino)-7-oxaspiro[5.6]dodecan-3-yl)propanamide
• CAS: 1569043-59-9
• 化学式: C₃₆H₄₃N₃O₁₁
• 分子量: 693.751
• InChiKey: FAWXNNBDQQREAF-PTYLGAKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  50.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  216.14
• 氢给体数：
  8.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (S)-3-(4-hydroxyphenyl)-2-(carbobenzyloxyamino)-N-((1R,2S,3R,5S,6S,9R,10S)-1,2,9,10-tetrahydroxy-5-(carbobenzyloxyamino)-7-oxaspiro[5.6]dodecan-3-yl)propanamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以35%的产率得到(S)-2-amino-N-((1R,2S,3R,5S,6S,9R,10S)-5-amino-1,2,9,10-tetrahydro-xy-7-oxaspiro[5.6]dodecan-3-yl)-3-(4-hydroxyphenyl)propanamide
  参考文献：
  名称：

  Rigid spiroethers targeting the decoding center of the bacterial ribosome

  摘要：

  Continuing our efforts towards understanding the principles governing ribosomal recognition and function, we have synthesized and evaluated a series of diversely functionalized 5,6-, 6,6- and 7,6- spiroethers. These compounds successfully mimic natural aminoglycosides regarding their binding to the decoding center of the bacterial ribosome. Their potential to inhibit prokaryotic protein production in vitro along with their antibacterial potencies have also been examined. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.068
• 作为产物：
  描述：

  dibenzyl ((3aR,4S,5S,7R,7aS)-4-(allyloxy)-4-(but-3-en-1-yl)hexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyl)dicarbamate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 四氧化锇 、 sodium hydride 、 碳酸氢钠 、 N-甲基吗啉氧化物 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 49.0h， 生成 (S)-3-(4-hydroxyphenyl)-2-(carbobenzyloxyamino)-N-((1R,2S,3R,5S,6S,9R,10S)-1,2,9,10-tetrahydroxy-5-(carbobenzyloxyamino)-7-oxaspiro[5.6]dodecan-3-yl)propanamide
  参考文献：
  名称：

  Rigid spiroethers targeting the decoding center of the bacterial ribosome

  摘要：

  Continuing our efforts towards understanding the principles governing ribosomal recognition and function, we have synthesized and evaluated a series of diversely functionalized 5,6-, 6,6- and 7,6- spiroethers. These compounds successfully mimic natural aminoglycosides regarding their binding to the decoding center of the bacterial ribosome. Their potential to inhibit prokaryotic protein production in vitro along with their antibacterial potencies have also been examined. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.068