3-O-[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-[β-D-glucopyranosyl]cholestan
• 英文别名: Glc-cholestanol；5α-cholestan-3β-yl-β-D-glucopyranoside；5α-Cholestan-3β-yl-β-D-glucopyranosid；(2R,3R,4S,5S,6R)-2-[[(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]-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₃₃H₅₈O₆
• 分子量: 550.82
• InChiKey: WCKMVARSQFCTKY-DQWBMVLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-O-[β-D-glucopyranosyl]cholestan 在 吡啶 、 4,4'-双甲氧基三苯甲基氯 、 三氧化硫 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 168.0h， 生成 5α-cholestan-3β-yl β-D-glucopyranoside-6-sulfate triethylammonium salt
  参考文献：
  名称：

  Synthesis of 5α-Cholestane Type Glycoside Sulfates

  摘要：

  类固醇糖苷硫酸酯的合成，既在类固醇骨架上进行硫酸化，又在糖部分进行硫酸化。从3β-(2-四氢吡喃氧基)-5α-胆甾-6α-醇（I）制备了5α-胆甾烷-3β,6α-二醇-6-β-D-葡萄糖苷-3-硫酸盐V和3-β-D-葡萄糖苷-6-硫酸盐XI的钠盐，使用乙酰基和甲氧甲基基团进行临时保护。首先在孕烷系列中检查了糖部分的硫酸化，并制备了3β-(β-D-葡萄糖吡喃基氧基)孕-5-烯-20-酮-6'-硫酸盐XXVI和4'-硫酸盐2',3'-二乙酸酯XXVII的三乙基铵盐。将该方法应用于胆甾衍生物上，得到了5α-胆甾-3β-基β-D-葡萄糖吡喃苷-6-硫酸盐XXXI的三乙基铵盐。

  DOI：

  10.1135/cccc19931180
• 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 甲醇 、 sodium methylate 、 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 53.0h， 生成 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

文献信息

• Completely β-Selective Glycosylation Using 3,6-<i>O</i>-(<i>o</i>-Xylylene)-Bridged Axial-Rich Glucosyl Fluoride
  作者：Yasunori Okada、Noriaki Asakura、Masafumi Bando、Yoshiki Ashikaga、Hidetoshi Yamada

  DOI：10.1021/ja301480g

  日期：2012.4.25

  A completely β-selective glycosylation that does not rely on neighboring group participation is described. The novelty of this work is the design of the glycosyl donor locked into the axial-rich form by the o-xylylene bridge between the 3-O and 6-O of d-glucopyranose. The synthesized 2,4-di-O-benzyl-3,6-O-(o-xylyene)glucopyranosyl fluoride could efficiently react with various alcohols in a SnCl(2)-AgB(C(6)F(5))(4)

  描述了一种不依赖于相邻基团参与的完全 β 选择性糖基化。这项工作的新颖之处在于设计的糖基供体通过 d-吡喃葡萄糖的 3-O 和 6-O 之间的邻二甲苯桥锁定为富含轴向的形式。合成的 2,4-di-O-benzyl-3,6-O-(o-xylyene) 吡喃葡萄糖基氟可以有效地与 SnCl(2)-AgB(C(6)F(5))( 4）催化体系。通过使用酸性和碱性分子筛的比较实验揭示了由糖基化和异构化循环组成的机制。实现的完美立体控制归因于富含轴向的构象和由原位生成的 HB(C(6)F(5))(4) 引起的收敛异构化的协同作用。
• Steinegger; Katz, Pharmaceutica Acta Helvetiae, 1947, vol. 22, p. 1,5
  作者：Steinegger、Katz

  DOI：——

  日期：——
• The Preparation of Cholestanol Glucosides with All Four Possible Configurations of the Glucoside Link
  作者：R. P. Linstead

  DOI：10.1021/ja01864a034

  日期：1940.7
• Synthesis of 5α-Cholestane Type Glycoside Sulfates
  作者：Libuše Arnoštová、Ivan Černý、Vladimír Pouzar、Pavel Drašar

  DOI：10.1135/cccc19931180

  日期：——

  Synthesis of steroid glycoside sulfates sulfated both on the steroid skeleton and in sugar part are presented. Sodium salts of 5α-cholestane-3β,6α-diol 6-β-D-glucoside 3-sulfate V and 3-β-D-glucoside 6-sulfate XI were prepared from 3β-(2-tetrahydropyranyloxy)-5α-cholestan-6α-ol (I) using acetyl and methoxymethyl groups for temporary protection. Sulfation in the sugar part was at first checked in pregnane series and triethylammonium salts of 3β-(β-D-glucopyranosyloxy)pregn-5-en-20-one 6'-sulfate (XXVI) and 4'-sulfate 2',3'-diacetate XXVII were prepared. Application of the method on cholestane derivatives gave triethylammonium salt of 5α-cholestan-3β-yl β-D-glucopyranoside-6-sulfate (XXXI).

  类固醇糖苷硫酸酯的合成，既在类固醇骨架上进行硫酸化，又在糖部分进行硫酸化。从3β-(2-四氢吡喃氧基)-5α-胆甾-6α-醇（I）制备了5α-胆甾烷-3β,6α-二醇-6-β-D-葡萄糖苷-3-硫酸盐V和3-β-D-葡萄糖苷-6-硫酸盐XI的钠盐，使用乙酰基和甲氧甲基基团进行临时保护。首先在孕烷系列中检查了糖部分的硫酸化，并制备了3β-(β-D-葡萄糖吡喃基氧基)孕-5-烯-20-酮-6'-硫酸盐XXVI和4'-硫酸盐2',3'-二乙酸酯XXVII的三乙基铵盐。将该方法应用于胆甾衍生物上，得到了5α-胆甾-3β-基β-D-葡萄糖吡喃苷-6-硫酸盐XXXI的三乙基铵盐。
• 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.