dibenzyl ((1S,3R,4S,5R,6S,9R,10S)-4,5,9,10-tetrahydroxy-7-oxaspiro[5.6]dodecane-1,3-diyl)dicarbamate | 1261084-76-7

• 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: dibenzyl ((1S,3R,4S,5R,6S,9R,10S)-4,5,9,10-tetrahydroxy-7-oxaspiro[5.6]dodecane-1,3-diyl)dicarbamate
• CAS: 1261084-76-7
• 化学式: C₂₇H₃₄N₂O₉
• 分子量: 530.575
• InChiKey: WDVXWXVSQXOXLO-ZJCALNSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.97
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  166.81
• 氢给体数：
  6.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  dibenzyl ((1S,3R,4S,5R,6S,9R,10S)-4,5,9,10-tetrahydroxy-7-oxaspiro[5.6]dodecane-1,3-diyl)dicarbamate 在 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 sodium cyanoborohydride 、 溶剂黄146 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (1R,2S,3R,5S,6S,9R,10S)-5-amino-3-(((S)-2-amino-3-(4-hydroxyphenyl)propyl)amino)-7-oxaspiro[5.6]do-decane-1,2,9,10-tetraol
  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：

  在 盐酸 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 6.0h， 生成 dibenzyl ((1S,3R,4S,5R,6S,9R,10S)-4,5,9,10-tetrahydroxy-7-oxaspiro[5.6]dodecane-1,3-diyl)dicarbamate
  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

文献信息

• Second generation analogs of rigid 6,7-spiro scaffolds targeting the bacterial ribosome
  作者：Christos I. Stathakis、Ioannis Mavridis、Georgia Kythreoti、Athanasios Papakyriakou、Ioannis A. Katsoulis、Thomas Cottin、Panoula Anastasopoulou、Dionisios Vourloumis

  DOI：10.1016/j.bmcl.2010.10.001

  日期：2010.12

  Previous work from our group described the synthesis and biological evaluation of new rigid, 6,6- and 6,7-spiro aminoglycosidic scaffolds targeting the bacterial ribosome. Herein we describe an improved synthetic protocol for their construction, and extend our study by further amino-functionalization of their 6,7-spiro analogs. The synthetic strategy, preparation and evaluation of some representative examples are reported. (C) 2010 Elsevier Ltd. All rights reserved.