[(2R,3R,4S,6R)-3-[[(3aR,4R,6S,7aS)-2-hydroxy-2,4-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-2-methyl-6-phenylmethoxyoxan-4-yl] acetate | 1054636-82-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4S,6R)-3-[[(3aR,4R,6S,7aS)-2-hydroxy-2,4-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-2-methyl-6-phenylmethoxyoxan-4-yl] acetate
• CAS: 1054636-82-6
• 化学式: C₂₃H₃₂O₉
• 分子量: 452.502
• InChiKey: UELBALPIMUWSTH-ZPJFOJFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,6R)-3-[[(3aR,4R,6S,7aS)-2-hydroxy-2,4-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-2-methyl-6-phenylmethoxyoxan-4-yl] acetate 在 水 作用下， 生成 phenylmethyl 3-O-acetyl-4-O-[3-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranosyl]-2,6-dideoxy-β-D-ribo-hexopyranoside
  参考文献：
  名称：

  A Direct Comparison of the Anticancer Activities of Digitoxin MeON-Neoglycosides and O-Glycosides

  摘要：

  Digitoxin is a cardiac glycoside currently being investigated for potential use in oncology; however, an investigation of anticancer activity as a function, of oligosaccharide chain length has not yet been performed. We generated mono-, di-, and tri-O-digitoxoside derivatives, of digitoxin and compared their activities to the corresponding MeON-neoglycosides. Both classes of cardenolide derivatives display comparable oligosaccharide chain length-dependent cytotoxicity toward human cancer cell lines. Further investigation revealed that both classes of compounds induce caspase-9-mediated apoptosis in non-small cell lung cancer cells (NCI-H460). Because O-glycosides and MeON-neoglycosides share a similar mode of action, the convenience of MeON-neoglycosylation could be exploited in future SAR work to rapidly survey large numbers of carbohydrates to prioritize selected O-glycoside candidates for traditional synthesis.

  DOI：

  10.1021/ml1000933
• 作为产物：
  描述：

  原乙酸三甲酯 、 phenylmethyl 3-O-acetyl-4-O-[2,6-dideoxy-β-D-ribo-hexopyranosyl]-2,6-dideoxy-β-D-ribo-hexopyranoside 在 对甲苯磺酸 作用下， 生成 [(2R,3R,4S,6R)-3-[[(3aR,4R,6S,7aS)-2-hydroxy-2,4-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-2-methyl-6-phenylmethoxyoxan-4-yl] acetate
  参考文献：
  名称：

  A Direct Comparison of the Anticancer Activities of Digitoxin MeON-Neoglycosides and O-Glycosides

  摘要：

  Digitoxin is a cardiac glycoside currently being investigated for potential use in oncology; however, an investigation of anticancer activity as a function, of oligosaccharide chain length has not yet been performed. We generated mono-, di-, and tri-O-digitoxoside derivatives, of digitoxin and compared their activities to the corresponding MeON-neoglycosides. Both classes of cardenolide derivatives display comparable oligosaccharide chain length-dependent cytotoxicity toward human cancer cell lines. Further investigation revealed that both classes of compounds induce caspase-9-mediated apoptosis in non-small cell lung cancer cells (NCI-H460). Because O-glycosides and MeON-neoglycosides share a similar mode of action, the convenience of MeON-neoglycosylation could be exploited in future SAR work to rapidly survey large numbers of carbohydrates to prioritize selected O-glycoside candidates for traditional synthesis.

  DOI：

  10.1021/ml1000933