| 1256288-73-9

• 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
• CAS: 1256288-73-9
• 化学式: C₄₅H₈₈O₆Si₄
• 分子量: 837.532
• InChiKey: ZXEIUYHVHUWLMT-BHMPLXLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.65
• 重原子数：
  55.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  D-葡萄糖 在 碘代三甲硅烷 、 四丁基碘化铵 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 52.83h， 生成 cholesteryl 2,3,4,6-tetra-O-trimethylsilyl-α-D-glucopyranoside 、
  参考文献：
  名称：

  胆固醇糖苷信号通过巨噬细胞诱导性C型凝集素（小分子）的碳水化合物识别结构域

  摘要：

  胆固醇α- D-葡萄糖苷（αGCs）是引起癌症的人类病原体幽门螺杆菌的独特代谢产物。通过巨噬细胞可诱导的C型凝集素（Mincle）的信号传导和促炎反应的诱导，它们被认为在胃萎缩的发生中起作用。本文中，我们制备了第一个甾基D-葡萄糖苷文库，并确定它们优先通过人Mincle的碳水化合物识别结构域而不是氨基酸共有基序发出信号。脂化的甾基D-葡萄糖苷具有增强的Mincle激动剂活性，C18胆固醇基6 - O-酰基-α- D-葡萄糖苷（2c）是人类单核细胞最有效的激活剂。尽管表现出强烈的Mincle信号转导，但西多（5b）和豆甾醇（6b）导致原代细胞中较差的炎症反应，表明Mincle是预防幽门螺杆菌介导的炎症和癌症的潜在治疗靶标。

  DOI：

  10.1039/d0ob02342f

文献信息

• 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.
• Tandem Glycosyl Iodide Glycosylation and Regioselective Enzymatic Acylation Affords 6-<i>O</i>-Tetradecanoyl-α-<scp>d</scp>-cholesterylglycosides
  作者：Ryan A. Davis、James C. Fettinger、Jacquelyn Gervay-Hague

  DOI：10.1021/jo501371h

  日期：2014.9.5

  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.