tigogenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)-4,6-di-O-benzylidene-β-D-galactopyranoside | 1599463-40-7

• 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: tigogenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)-4,6-di-O-benzylidene-β-D-galactopyranoside
• CAS: 1599463-40-7
• 化学式: C₅₂H₇₄O₁₅
• 分子量: 939.151
• InChiKey: IWTDFTLWDDVLFY-WSYXFZJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.94
• 重原子数：
  67.0
• 可旋转键数：
  8.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  172.97
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  tigogenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)-4,6-di-O-benzylidene-β-D-galactopyranoside 、 2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl trichloroacetimidate-¹C₄ 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以66%的产率得到tigogenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)-[2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl-(1→3)]-4,6-di-O-benzylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Efficient Synthesis and Antitumor Activities of Indioside E Analogs

  摘要：

  An efficient synthesis of seven analogs of a naturally occurring saponin, indioside E, is described. The synthesis used a 3,4,6-O-protected D-galactopyranosyl thioglycoside as the key intermediate to enable regioselective glycosylation and one-pot multistep reactions. Antitumor activities of the synthetic saponins against a human hepatocellular carcinoma cell line BEL-7402 and a human breast adenocarcinoma cell line MCF-7 were evaluated by means of the CCK-8 assay. Analogs carrying trisaccharides with the D-xylopyranose in indioside E substituted with a D-ribopyranose and an L-arabinopyranose or with its diosgenin aglycon replaced with tigogenin exhibited similar antitumor activities as indioside E, but not other analogs.

  DOI：

  10.1080/07328303.2014.900564
• 作为产物：
  描述：

  在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以610 mg的产率得到tigogenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)-4,6-di-O-benzylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Efficient Synthesis and Antitumor Activities of Indioside E Analogs

  摘要：

  An efficient synthesis of seven analogs of a naturally occurring saponin, indioside E, is described. The synthesis used a 3,4,6-O-protected D-galactopyranosyl thioglycoside as the key intermediate to enable regioselective glycosylation and one-pot multistep reactions. Antitumor activities of the synthetic saponins against a human hepatocellular carcinoma cell line BEL-7402 and a human breast adenocarcinoma cell line MCF-7 were evaluated by means of the CCK-8 assay. Analogs carrying trisaccharides with the D-xylopyranose in indioside E substituted with a D-ribopyranose and an L-arabinopyranose or with its diosgenin aglycon replaced with tigogenin exhibited similar antitumor activities as indioside E, but not other analogs.

  DOI：

  10.1080/07328303.2014.900564