26-O-tert-butyldiphenylsilyl-3β-O-(3,6-di-O-benzoyl-β-D-glucopyranosyl)-(25R)-furost-5-en | 743423-63-4

• 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-O-tert-butyldiphenylsilyl-3β-O-(3,6-di-O-benzoyl-β-D-glucopyranosyl)-(25R)-furost-5-en
• CAS: 743423-63-4
• 化学式: C₆₃H₈₀O₁₀Si
• 分子量: 1025.41
• InChiKey: LXBGNYNLYZKYBX-PPPBQHQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.49
• 重原子数：
  74.0
• 可旋转键数：
  15.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  129.98
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate 、 26-O-tert-butyldiphenylsilyl-3β-O-(3,6-di-O-benzoyl-β-D-glucopyranosyl)-(25R)-furost-5-en 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 生成 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
  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：

  薯蓣皂素 在 咪唑 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三氯化铝 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 氯仿 为溶剂， 反应 50.33h， 生成 26-O-tert-butyldiphenylsilyl-3β-O-(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