diosgenyl β-D-glucopyranosyl-(1->2)-β-D-glucopyranoside | 94805-85-3

• 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: diosgenyl β-D-glucopyranosyl-(1->2)-β-D-glucopyranoside
• 英文别名: (25R)-3β-(O²-β-D-glucopyranosyl-β-D-glucopyranosyloxy)-spirost-5-ene；(25R)-3β-(O²-β-D-Glucopyranosyl-β-D-glucopyranosyloxy)-spirost-5-en；(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 94805-85-3
• 化学式: C₃₉H₆₂O₁₃
• 分子量: 738.913
• InChiKey: SOSXYUIKBSZONB-MKCQZNCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  52
• 可旋转键数：
  6
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  197
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  diosgenyl 4,6-O-benzylidene-β-D-glucopyranoside 在 molecular sieve 、 三氟化硼乙醚 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 diosgenyl β-D-glucopyranosyl-(1->2)-β-D-glucopyranoside
  参考文献：
  名称：

  Chemical Synthesis of Several 2'-O-, 3'-O-Glycosylated Diosgenyl β-D-Glucopyranosides

  摘要：

  Six 2'-O-, 3'-O-glycosylated diosgenyl beta-D-glucopyranosides (4-9), which have a typical structural pattern of diosgenyl saponins, were synthesized; their synthetic routes are discussed.

  DOI：

  10.1080/07328309908544058

文献信息

• Synthesis of novel spirostanic saponins and their cytotoxic activity
  作者：Juan C. Hernández、Francisco León、Ignacio Brouard、Fernando Torres、Sara Rubio、José Quintana、Francisco Estévez、Jaime Bermejo

  DOI：10.1016/j.bmc.2007.10.089

  日期：2008.2.15

  This study was carried out to assess the cytotoxicity of several new synthetic steroidal saponins against the human myeloid leukemia cell lines (HL-60 and U937) and against human melanoma cells (SK-MEL-1). Several diosgenyl glycosides analyzed showed strong cell growth inhibition which was associated with alterations in cell cycle progression and induction of apoptosis. Studies of cytochrome c release and caspase-9 activation suggest a main role of the intrinsic pathway of apoptosis in the mechanism of cytotoxicity caused by this kind of compounds. (c) 2007 Elsevier Ltd. All rights reserved.
• Chemical Synthesis of Several 2'-<i>O</i>-, 3'-<i>O</i>-Glycosylated Diosgenyl β-D-Glucopyranosides
  作者：Chuan Li、Biao Yu、Yongzheng Hui

  DOI：10.1080/07328309908544058

  日期：1999.1

  Six 2'-O-, 3'-O-glycosylated diosgenyl beta-D-glucopyranosides (4-9), which have a typical structural pattern of diosgenyl saponins, were synthesized; their synthetic routes are discussed.