diosgenyl 2,4-di-O-(2,3,4-tri-O-pivaloyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-β-D-glucopyranoside | 335591-75-8

• 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 2,4-di-O-(2,3,4-tri-O-pivaloyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-β-D-glucopyranoside
• 英文别名: diosgen-3-yl 2,4-di-O-(2,3,4-tri-O-pivaloyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-β-D-glucopyranoside；[(2R,3R,4S,5R,6R)-4-(2,2-dimethylpropanoyloxy)-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-3,5-bis[[(2S,3R,4R,5S,6S)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-methyloxan-2-yl]oxy]oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 335591-75-8
• 化学式: C₈₅H₁₃₆O₂₄
• 分子量: 1542.0
• InChiKey: GEDFMPAWKPVGBN-YKZSITEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.1
• 重原子数：
  109
• 可旋转键数：
  31
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  284
• 氢给体数：
  0
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  diosgenyl 2,4-di-O-(2,3,4-tri-O-pivaloyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-β-D-glucopyranoside 在 Oxone 、 disodium ethylenediaminetetraacetic acid 、 碳酸氢钠 作用下， 以 氯仿 、 水 、 丙酮 为溶剂， 生成 (25R)-3β-[2,4-di-O-(2,3,4-tri-O-pivaloyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-β-D-glucopyranosyloxy]-5,6-epoxy-spirostan-16α-ol 、 (25R)-3β-[2,4-di-O-(2,3,4-tri-O-pivaloyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-β-D-glucopyranosyloxy]-5,6-epoxy-spirostan-16α-ol
  参考文献：
  名称：

  Facile Conversion of Spirostan Saponin into Furostan Saponin:  Synthesis of Methyl Protodioscin and Its 26-Thio-analogue

  摘要：

  A facile approach for the conversion of a spirostan saponin into its furostan counterpart, as illustrated by the transformation of dioscin to methyl protodioscin (and its 26-thio-analogue), has been developed.

  DOI：

  10.1021/ol060594w
• 作为产物：
  描述：

  2,3,4-tri-O-pivaloyl-α-L-rhamnopyranosyl trichloroacetimidate 、 diosgenyl 3,6-di-O-pivaloyl-β-D-glucopyranoside 在 4 A molecular sieve 、 叔丁基二甲硅基三氟甲磺酸酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到diosgenyl 2,4-di-O-(2,3,4-tri-O-pivaloyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-β-D-glucopyranoside
  参考文献：
  名称：

  Facile Conversion of Spirostan Saponin into Furostan Saponin:  Synthesis of Methyl Protodioscin and Its 26-Thio-analogue

  摘要：

  A facile approach for the conversion of a spirostan saponin into its furostan counterpart, as illustrated by the transformation of dioscin to methyl protodioscin (and its 26-thio-analogue), has been developed.

  DOI：

  10.1021/ol060594w

文献信息

• An improved synthesis of the saponin, polyphyllin D
  作者：Bing Li、Biao Yu*、Yongzheng Hui*、Ming Li、Xiuwen Han、Kwok-Pui Fung

  DOI：10.1016/s0008-6215(01)00014-3

  日期：2001.3

  Polyphyllin D, namely diosgenyl alpha -L-rhamnopyranosyl-(1->2)-[(alpha -L-arabinofuranosyl)-(1->4)]-beta -D-glucopyranoside, was synthesized from diosgenyl-beta -D-glucopyranoside in four steps and in 30% overall yield, taking advantage of regioselective pivaloylation and alpha -L-rhamnopyranosylation reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.