cholesterylglycoside | 26671-80-7

• 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: cholesterylglycoside
• 英文别名: cholesteryl glucoside；1-O-(3beta-Cholesteryl)-D-glucopyranose；(3R,4S,5S,6R)-2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 26671-80-7
• 化学式: C₃₃H₅₆O₆
• 分子量: 548.804
• InChiKey: FSMCJUNYLQOAIM-URQIRGSUSA-N

物化性质

• 沸点：
  658.3±55.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  1-anthroylnitrile 、 cholesterylglycoside 在 奎宁环 作用下， 以 乙腈 为溶剂， 反应 0.33h， 生成
  参考文献：
  名称：

  Murui, Tateo; Wanaka, Kou, Bioscience, Biotechnology and Biochemistry, 1993, vol. 57, # 4, p. 614 - 617

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,3R,4S,5R)-2-((benzoyloxy)methyl)-6-(((3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 cholesterylglycoside
  参考文献：
  名称：

  Cholesterol-derived novel anti-apoptotic agents on the structural basis of ginsenoside Rk1

  摘要：

  Design and synthesis of cholesterol-derived anti-apoptotic agents were described. The synthesized cholesterol analogs designed on the structural basis of ginsenoside Rk1 inhibited the undesirable apoptosis of human endothelial cells, which are induced by a vascular injury. In particular, analogue 1 possessing 4,6di-O-acetyl-2,3-dideoxyhex-2-enopyran linked to hydroxyl group of cholesterol exhibited the most effective anti-apoptotic activities at both 5 and 10 mu g/ml. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.071

文献信息

• Sterol glucoside toxins
  申请人：——

  公开号：US20040048810A1

  公开（公告）日：2004-03-11

  The invention relates to the identification of sterol glucoside toxins, and provides methods for detecting and detoxifying the compounds, as well as therapeutic methods for treating subjects exposed to such toxins. In alternative embodiments, the toxins may for example include beta-sitostrol-beta-D-glucoside (5-cholesten-24b-ethyl-3b-ol-D-glucoside) or cholesterol glucoside (5-cholesten-3b-ol-3b-D-glucoside).

  本发明涉及甾醇葡萄糖苷毒素的鉴定，并提供检测和解毒该化合物的方法，以及治疗暴露于此类毒素的受试者的治疗方法。在另一种实施方式中，毒素可以包括β-谷甾醇-β-D-葡萄糖苷（5-胆甾-24b-乙基-3b-醇-D-葡萄糖苷）或胆固醇葡萄糖苷（5-胆甾-3b-醇-3b-D-葡萄糖苷）等。
• Direct Glycosylation of Bioactive Small Molecules with Glycosyl Iodide and Strained Olefin as Acid Scavenger
  作者：Xiangying Gu、Lin Chen、Xin Wang、Xiao Liu、Qidong You、Wenwei Xi、Li Gao、Guohua Chen、Yue-Lei Chen、Bing Xiong、Jingkang Shen

  DOI：10.1021/jo402551x

  日期：2014.2.7

  A new strategy for diversity-oriented direct glycosylation of bioactive small molecules was developed. This reaction features (-)-beta-pinene as acid scavenger and work with glycosyl iodides under mild conditions. With the aid of RP-HPLC and chiral SFC separation techniques, the new direct glycosylation proved effective at gram scale on bioactive small molecules including AZD6244, podophyllotoxin, paclitaxel, and docetaxel. Interesting glycoside derivatives were efficiently created with good yields and 1,2-cis selectivity.
• STEROL GLUCOSIDE TOXINS
  申请人：THE UNIVERSITY OF BRITISH COLUMBIA

  公开号：EP1334368A2

  公开（公告）日：2003-08-13
• US8497123B2
  申请人：——

  公开号：US8497123B2

  公开（公告）日：2013-07-30
• [EN] STEROL GLUCOSIDE TOXINS<br/>[FR] TOXINES DE STEROL GLUCOSIDE
  申请人：UNIV BRITISH COLUMBIA

  公开号：WO2002037122A2

  公开（公告）日：2002-05-10

  The invention relates to the identification of sterol glucoside toxins, and provides methods for detecting and detoxifying the compounds, as well as therapeutic methods for treating subjects exposed to such toxins. In alternative embodiments, the toxins may for example include beta-sitostrol-beta-D-glucoside (5-cholesten-24b-ethyl-3b-ol-D-glucoside) or cholesterol glucoside (5-cholesten-3b-ol-3b-D-glucoside).