(1R,4R,6R,9R,11S,14S,15R,17R,20R,22S)-1,22-dimethoxy-2,5,7,10,13,16,18,21-octaoxa-6,7-diphenyltetracyclo[12.8.0.0^4,9.0^15,20]docosane-3,12-dione

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: (1R,4R,6R,9R,11S,14S,15R,17R,20R,22S)-1,22-dimethoxy-2,5,7,10,13,16,18,21-octaoxa-6,7-diphenyltetracyclo[12.8.0.0^4,9.0^15,20]docosane-3,12-dione
• 英文别名: (1R,4R,6R,9R,11S,14S,15R,17R,20R,22S)-11,22-dimethoxy-6,17-diphenyl-2,5,7,10,13,16,18,21-octaoxatetracyclo[12.8.0.04,9.015,20]docosane-3,12-dione
• 化学式: C₂₈H₃₀O₁₂
• 分子量: 558.539
• InChiKey: GCGDGNKHSBUHOA-LZOIBTTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  40
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 在 pyridinium chlorochromate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 48.0h， 以44%的产率得到(1R,4R,6R,9R,11S,14S,15R,17R,20R,22S)-1,22-dimethoxy-2,5,7,10,13,16,18,21-octaoxa-6,7-diphenyltetracyclo[12.8.0.0^4,9.0^15,20]docosane-3,12-dione
  参考文献：
  名称：

  Sugar bislactones by one-step oxidative dimerisation with pyridinium chlorochromate versus regioselective oxidation of vicinal diols

  摘要：

  Synthesis of 10-membered bislactones by PCC oxidation of methyl 2,6-di-O-pivaloyl-alpha-D-glucopyranoside and methyl 4,6-O-benzylidene-alpha-D-glucopyranoside is described, with emphasis on their structure elucidation using the information gained by combination of NMR spectroscopic techniques with X-ray diffraction data. In alternative, the use of PCC and PCC adsorbed on silica gel or alumina for the regioselective oxidation of vicinal diols in sugars is also reported. Both bislactones showed antifungal activity against Candida albicans, and were slightly active against the bacteria Bacillus subtilis. The bislactone presenting pivaloyl protecting groups also promoted some growth inhibition of Staphylococcus aureus. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.06.002