26-hydroxy-3β-O-[2,4-di-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,6-di-O-benzoyl-β-D-glucopyranosyl]-(25R)-furost-5-en | 743423-65-6

• 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: 26-hydroxy-3β-O-[2,4-di-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,6-di-O-benzoyl-β-D-glucopyranosyl]-(25R)-furost-5-en
• CAS: 743423-65-6
• 化学式: C₇₁H₉₄O₂₄
• 分子量: 1331.51
• InChiKey: IJYJNADCEHZTMF-VSWWWTBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.03
• 重原子数：
  95.0
• 可旋转键数：
  21.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  295.24
• 氢给体数：
  1.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  26-hydroxy-3β-O-[2,4-di-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,6-di-O-benzoyl-β-D-glucopyranosyl]-(25R)-furost-5-en 在 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 以76%的产率得到3β-O-[2,4-di-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyl]-26-hydroxy-(25R)-5-en
  参考文献：
  名称：

  Synthesis of bidesmosidic dihydrodiosgenin saponins bearing a 3-O-β-chacotriosyl moiety

  摘要：

  3-O-beta-Chacotriosyl-26-O-beta-D-glucopyranosyl-(25R)-furost-5-en (1), a mimic of the antitumor active proto-dioscin, was concisely synthesized from diosgenin in a linear nine steps and in 17% overall yield. Its congeners with a alpha-L-rhamnopyranosyl, beta-lactosyl, or without a substituent at the 26-OH (13-15) were also prepared. Compound 1, as well as 13-15, did not show any inhibition against tumor cells, implying that proto-dioscin might be also inactive, but readily converted into the antitumor active dioscin. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.04.014
• 作为产物：
  描述：

  26-O-tert-butyldiphenylsilyl-3β-O-[2,4-di-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,6-di-O-benzoyl-β-D-glucopyranosyl]-(25R)-furost-5-en 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以0.87 g的产率得到26-hydroxy-3β-O-[2,4-di-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,6-di-O-benzoyl-β-D-glucopyranosyl]-(25R)-furost-5-en
  参考文献：
  名称：

  Synthesis of bidesmosidic dihydrodiosgenin saponins bearing a 3-O-β-chacotriosyl moiety

  摘要：

  3-O-beta-Chacotriosyl-26-O-beta-D-glucopyranosyl-(25R)-furost-5-en (1), a mimic of the antitumor active proto-dioscin, was concisely synthesized from diosgenin in a linear nine steps and in 17% overall yield. Its congeners with a alpha-L-rhamnopyranosyl, beta-lactosyl, or without a substituent at the 26-OH (13-15) were also prepared. Compound 1, as well as 13-15, did not show any inhibition against tumor cells, implying that proto-dioscin might be also inactive, but readily converted into the antitumor active dioscin. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.04.014