3-O-[2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl]cholestan | 1352548-77-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3-O-[2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl]cholestan
• CAS: 1352548-77-6
• 化学式: C₈₈H₉₆O₁₈
• 分子量: 1441.72
• InChiKey: RNRTWDIXHGQMCZ-DAXUJLRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.17
• 重原子数：
  106.0
• 可旋转键数：
  25.0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  221.02
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  3-O-[2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl]cholestan 在 甲醇 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到3-O-[α-D-glucopyranosyl-(1→4)-α-D-glucopyranosyl]cholestan
  参考文献：
  名称：

  Antifungal activity of 2α,3β-functionalized steroids stereoselectively increases with the addition of oligosaccharides

  摘要：

  Invasive fungal infections pose a significant problem to the immune-compromised. Moreover, increased resistance to common antifungals requires development of novel compounds that can be used to treat invasive fungal infections. Naturally occurring steroidal glycosides have been shown to possess a range of functional antimicrobial properties, but synthetic methodology for their development hinders thorough exploration of this class of molecules and the structural components required for broad spectrum antifungal activity. In this report, we outline a novel approach to the synthesis of glycoside-linked functionalized 2 alpha,3 beta-cholestane and spirostane molecules and present data from in vitro screenings of the antifungal activities against human fungal pathogens and as well as mammalian cell toxicity of these derivatives. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.015
• 作为产物：
  描述：

  O-(tetra-O-benzoyl-α-D-glucopyranosyl-(1→4)-tri-O-benzoyl-α-D-glucopyranosyl)trichloroacetimdate 、 3β-胆甾烷醇 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以51%的产率得到3-O-[2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl]cholestan
  参考文献：
  名称：

  Antifungal activity of 2α,3β-functionalized steroids stereoselectively increases with the addition of oligosaccharides

  摘要：

  Invasive fungal infections pose a significant problem to the immune-compromised. Moreover, increased resistance to common antifungals requires development of novel compounds that can be used to treat invasive fungal infections. Naturally occurring steroidal glycosides have been shown to possess a range of functional antimicrobial properties, but synthetic methodology for their development hinders thorough exploration of this class of molecules and the structural components required for broad spectrum antifungal activity. In this report, we outline a novel approach to the synthesis of glycoside-linked functionalized 2 alpha,3 beta-cholestane and spirostane molecules and present data from in vitro screenings of the antifungal activities against human fungal pathogens and as well as mammalian cell toxicity of these derivatives. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.015