cholesterol-3β-yl α-L-rhamnopyranosyl-(1->4)-[α-L-rhamnopyranosyl-(1->2)]-α-D-glucopyranoside

• 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: cholesterol-3β-yl α-L-rhamnopyranosyl-(1->4)-[α-L-rhamnopyranosyl-(1->2)]-α-D-glucopyranoside
• 英文别名: (2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6S)-6-[[(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]-4-hydroxy-2-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• 化学式: C₄₅H₇₆O₁₄
• 分子量: 841.09
• InChiKey: YAEVVVONMGQOPC-VJEHPRFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  59
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  217
• 氢给体数：
  8
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  1,2,3,4,6-alpha-D-葡萄糖五乙酸酯 在 三氟化硼乙醚 氢氧化钾 、 四(三苯基膦)钯 、 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 6.0h， 生成 cholesterol-3β-yl α-L-rhamnopyranosyl-(1->4)-[α-L-rhamnopyranosyl-(1->2)]-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of neosaponins having an α- l -rhamnopyranosyl-(1→4)-[α- l -rhamnopyranosyl-(1→2)]- d -glucopyranosyl glyco-linkage

  摘要：

  To verify the role of the alpha -L-rhamnopyranosyl-(1 --> 4)-[alpha -L-rhamnopyranosyl-( 1 -->2)]-beta -D-glucopyranosyl (chacotriosyl) moiety of steroidal glycosides from Solaum plants in their antitumor and antivirus activities, chacotriosides of diosgenin, cholesterol, and glycrrhetic acid were synthesized by developing our trans-oligoglycosidation. The chacotriosyl trichloroacetimidate was linked to the aglycones to afford neoglycosides as a mixture of alpha and beta anomers, that was easily separated with ODS chromatography. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00173-3

文献信息

• Synthesis of neosaponins and neoglycolipids containing a chacotriosyl moiety
  作者：Hiroyuki Miyashita、Tsuyoshi Ikeda、Toshihiro Nohara

  DOI：10.1016/j.carres.2007.06.008

  日期：2007.11

  -(1-->4)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyr anose (chacotriose) is the oligosaccharide moiety of dioscin. Chacotriosyl trichloroacetimidate was synthesized from d-glucose and l-rhamnose, and glycosylated to mevalonate (diosgenin, cholesterol, and glycyrrhetic acid) to yield dioscin and neosaponins. In order to simplify the structure of the aglycone part, the mevalonate moiety was replaced

  α-L-鼠李吡喃糖基-（1→4）-[α-L-鼠李吡喃糖基-（1→2）]-β-D-吡喃葡萄糖（chacotriose）是薯os的寡糖部分。Chacotriosyl trichloroacetimidate由d-葡萄糖和l-鼠李糖合成，并被糖基化为甲羟戊酸酯（洋地黄毒苷，胆固醇和甘草次酸），生成薯di皂苷和新皂苷。为了简化糖苷配基部分的结构，将甲羟戊酸酯部分替换为模仿糖基神经酰胺的双链新糖脂。细胞毒性试验表明，天然存在的β-形式的糖苷键很重要，薯di和最长链的新糖脂显示中等活性。