diosgenyl 2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzoyl-3-O-pivaloyl-β-D-glucopyranoside | 213753-23-2

• 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 2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzoyl-3-O-pivaloyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-4-(2,2-dimethylpropanoyloxy)-3-hydroxy-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-5-[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 213753-23-2
• 化学式: C₅₇H₈₀O₁₇
• 分子量: 1037.25
• InChiKey: ZFLPJGIPMHCJRK-NCZKVNAHSA-N

物化性质

• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  74
• 可旋转键数：
  17
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  207
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  diosgenyl 2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzoyl-3-O-pivaloyl-β-D-glucopyranoside 在 sodium hydroxide 、 4 Angstroem MS 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 2.5h， 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 吡啶 、 N-碘代丁二酰亚胺 、 4 Angstroem MS 、 三氟化硼乙醚 、 sodium methylate 、 silver trifluoromethanesulfonate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 diosgenyl 2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzoyl-3-O-pivaloyl-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

• Synthesis of a group of diosgenyl saponins with combined use of glycosyl trichloroacetimidate and thioglycoside donors
  作者：Hai Yu、Biao Yu、Xiangyang Wu、Yongzheng Hui、Xiuwen Han

  DOI：10.1039/a909218h

  日期：——

  With the combined use of glycosyl trichloroacetimidates and thioglycosides, a group of natural diosgenyl saponins (1–6) are efficiently synthesized, in either a stepwise or a ‘one-pot’ manner. The trichloroacetimidate is employed as an efficient temporary hydroxy protecting group in glycosylation with the glycosyl trichloroacetimidate. The intermolecular alkylthio-group transfer is demonstrated to be a common side-reaction during glycosylation with thioglycosides.

  通过结合使用糖基三氯乙亚胺酯和硫代糖苷，一系列天然薯蓣皂苷元的皂苷（1-6）被高效地合成，无论是逐步合成还是“一锅法”合成。三氯乙亚胺酯作为糖基化反应中糖基三氯乙亚胺酯的临时羟基保护组，表现出高效性。硫代糖苷参与的糖基化反应中，分子的烷硫基转移被证实是一种常见的副反应。
• 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 a group of diosgenyl saponins by a one-pot sequential glycosylation
  作者：Biao Yu、Hai Yu、Yongzheng Hui、Xiuwen Han

  DOI：10.1016/s0040-4039(99)01839-0

  日期：1999.12

  A group of natural diosgenyl saponins was synthesized in a highly efficient manner employing the 'one-pot sequential glycosylation' protocol with the combined use of glycosyl trichloroacetimidates and thioglycosides. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 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.