diosgenyl 4,6-O-benzylidene-β-D-glucopyranoside | 211797-89-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: diosgenyl 4,6-O-benzylidene-β-D-glucopyranoside
• 英文别名: (2R,4aR,6R,7R,8R,8aS)-2-phenyl-6-[(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]oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 211797-89-6
• 化学式: C₄₀H₅₆O₈
• 分子量: 664.88
• InChiKey: LPTGGWXZOPBNQS-LAWAGAANSA-N

物化性质

• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  48
• 可旋转键数：
  3
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  95.8
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diosgenyl 4,6-O-benzylidene-β-D-glucopyranoside 在 吡啶 、 sodium hydroxide 、 4 Angstroem MS 、 三氟化硼乙醚 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 9.0h， 生成 重楼皂苷I
  参考文献：
  名称：

  A facile synthetic approach to a group of structurally typical diosgenyl saponins

  摘要：

  A facile approach was developed for synthesizing an important group of plant diosgenyl saponins, three members (dioscin, polyphyllin D, and balanitin 7) with promising bioactivities were prepared. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01354-9
• 作为产物：
  描述：

  薯蓣皂素 在 N-碘代丁二酰亚胺 、 4 Angstroem MS 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 diosgenyl 4,6-O-benzylidene-β-D-glucopyranoside
  参考文献：
  名称：

  A facile synthetic approach to a group of structurally typical diosgenyl saponins

  摘要：

  A facile approach was developed for synthesizing an important group of plant diosgenyl saponins, three members (dioscin, polyphyllin D, and balanitin 7) with promising bioactivities were prepared. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01354-9

文献信息

• Glycosyl Trifluoroacetimidates. 2. Synthesis of Dioscin and Xiebai Saponin I
  作者：Biao Yu、Houchao Tao

  DOI：10.1021/jo026103c

  日期：2002.12.1

  Two trisaccharide steroidal saponins, dioscin (1) and Xiebai saponin 1 (2) with various bioactivities, were efficiently synthesized using the newly developed glycosyl N-phenyl trifluoroacetimidates (10-13) as glycosylation donors. Thus, dioscin was synthesized in five steps and a 33% overall yield from diosgenin and glycosyl trifluoroacetimidates (10 and 11). Xiebai saponin I was synthesized in eight steps and a 32% overall yield from laxogenin and glycosyl trifluoroacetimidates (10, 12, and 13), whereupon, the rare steroid laxogenin was prepared from diosgenin in four steps and an overall 69% yield. All the glycosylation reactions involved in the present syntheses demonstrated that glycosyl trifluoroacetimidates were successful donors comparable to the corresponding glycosyl trichloroacetimidates.
• Synthesis of three diosgenyl saponins: dioscin, polyphyllin D, and balanitin 7
  作者：Shaojiang Deng、Biao Yu、Yongzheng Hui、Hai Yu、Xiuwen Han

  DOI：10.1016/s0008-6215(99)00066-x

  日期：1999.4

  Dioscin, polyphyllin D, and balanitin 7, which belong to a group of structurally similar diosgenyl saponins with promising bioactivities, were synthesized by stepwise glycosylation. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 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.
• Synthesis of monomethylated dioscin derivatives and their antitumor activities
  作者：Ming Li、Xiuwen Han、Biao Yu

  DOI：10.1016/s0008-6215(02)00443-3

  日期：2003.1

  All possible eight monomethylated dioscin derivatives (1-8) were synthesized. Their inhibitory activities against P388 and A-549 cells were determined, and the results indicate that six of the eight hydroxyls of dioscin are the 'key polar groupings' for tumor inhibitory activities. (C) 2002 Elsevier Science Ltd. All rights reserved.