3-O-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl]cholestan

• 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-β-D-glucopyranosyl]cholestan
• 英文别名: Cholestanyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside；[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[[(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxan-2-yl]methyl benzoate
• 化学式: C₆₁H₇₄O₁₀
• 分子量: 967.253
• InChiKey: RGUKTCXWVNJSKJ-BTGQOJMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.1
• 重原子数：
  71
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-O-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl]cholestan 在 甲醇 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以88%的产率得到3-O-[β-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：

  1,2,3,4,6-戊-O-苯甲酰基-D-吡喃葡萄糖苷 在 potassium carbonate 、 C.I.酸性橙108 、 二甲基亚砜 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 52.0h， 生成 3-O-[2,3,4,6-tetra-O-benzoyl-β-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

文献信息

• Tetra-O-benzoylglucosylation: A New 1H Nuclear Magnetic Resonance Method for Determination of the Absolute Configuration of Secondary Alcohols
  作者：Mar Trujillo、Ezequiel Q. Morales、Jesus T. Vazquez

  DOI：10.1021/jo00101a023

  日期：1994.11

  A new method for determination of the absolute configuration of secondary alcohols based on the anisotropic effect and glycosylation-induced H-1 NMR shifts is described. The tetra-O-benzoyl-beta-glucosylation of secondary alcohols induces dramatic shifts in the aglycon H-1 NMR peaks. The differences between the proton chemical shifts of the D-glucosylated derivative and the free alcohol (Delta delta = delta(D) - delta(ROH)) or more significantly between their chemical shifts in the D- and L-glucosylated derivatives (Delta delta = delta(D) - delta(L)) are characteristic of the absolute configuration of the secondary chiral alcohol. Furthermore, in most cases the sign of the chemical shift difference of the carbinyl protons correlates with the absolute configuration of their carbons, namely positive or negative Delta delta are obtained for (R)- or (S)-carbinyl carbons, respectively. Moreover, this method involves the use of one enantiomer and generally a single derivatization is sufficient.
• Antifungal activity of 2α,3β-functionalized steroids stereoselectively increases with the addition of oligosaccharides
  作者：Amy Cammarata、Sunil Kumar Upadhyay、Branko S. Jursic、Donna M. Neumann

  DOI：10.1016/j.bmcl.2011.10.015

  日期：2011.12

  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.