cholesteryl α-D-galactopyranoside | 676485-39-5

• 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: cholesteryl α-D-galactopyranoside
• 英文别名: cholesteryl-α-D-galactopyranose；cholesteryl-α-D-galactoside；(2S,3R,4S,5R,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: 676485-39-5
• 化学式: C₃₃H₅₆O₆
• 分子量: 548.804
• InChiKey: FSMCJUNYLQOAIM-JYUGBWQRSA-N

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：

  肉豆蔻酸乙烯酯 、 cholesteryl α-D-galactopyranoside 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 96.0h， 以77%的产率得到cholesteryl-6-O-tetradecanoyl-α-D-galactopyranoside
  参考文献：
  名称：

  Tandem Glycosyl Iodide Glycosylation and Regioselective Enzymatic Acylation Affords 6-O-Tetradecanoyl-α-d-cholesterylglycosides

  摘要：

  A generalized synthesis of α-d-cholesterylglycosides has been achieved using one-pot per-O-trimethylsilyl glycosyl iodide glycosidation. Both cholesteryl α-d-glucopyranoside (αCG) and cholesteryl α-d-galactopyranoside were prepared in high yield. These compounds were further esterified using regioselective enzymatic acylation with tetradecanoyl vinyl ester to afford 6-O-tetradecanoyl-α-d-cholesteryl glucopyranoside (αCAG) of Helicobacter pylori and the corresponding galactose analogue in 66-78% overall yields from free sugars. The tandem step-economy sequence provides novel analogues to facilitate glycolipidomic profiling.

  DOI：

  10.1021/jo501371h
• 作为产物：
  描述：

  在 DOWEX 50WX₈-200 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以121 mg的产率得到cholesteryl α-D-galactopyranoside
  参考文献：
  名称：

  Two-Step Synthesis of the Immunogenic Bacterial Glycolipid BbGL1

  摘要：

  Chemical synthesis of a bacterial glycolipid BbGL1 is reported in two steps starting from per-O-TMS D-galactose. The key features are glycosyl iodide mediated beta-stereoselective glycosylation in the absence of neighboring group participation and regioselective acylation.

  DOI：

  10.1021/ol801780c

文献信息

• Glycosyl iodides. History and recent advances
  作者：Peter J. Meloncelli、Alan D. Martin、Todd L. Lowary

  DOI：10.1016/j.carres.2009.02.032

  日期：2009.6

  The use of glycosyl iodides as an effective method for the preparation of glycosides has had a recent resurgence in carbohydrate chemistry, despite its early roots in which these species were believed to be of limited use. Renewed interest in these species as glycosylating agents has been spurred by their demonstrated utility in the stereoselective preparation of O-glycosides, and other glycosylic compounds. This review provides a brief historical account followed by an examination of the use of glycosyl iodides in the synthesis of oligosaccharicles and other glycomimetics, including C-glycosylic compounds, glycosyl azides and N-glycosides. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.