10,6'-diphthalimido-6,2',3',4'-tetra-O-acetyl-10,6'-dideoxyaucubin | 927904-20-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 10,6'-diphthalimido-6,2',3',4'-tetra-O-acetyl-10,6'-dideoxyaucubin
• 英文别名: [(1S,4aR,5S,7aS)-7-[(1,3-dioxoisoindol-2-yl)methyl]-1-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(1,3-dioxoisoindol-2-yl)methyl]oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-5-yl] acetate
• CAS: 927904-20-9
• 化学式: C₃₉H₃₆N₂O₁₅
• 分子量: 772.719
• InChiKey: WZPYHCGCFRYSEY-XHEHMIQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  56
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  208
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  10,6'-diphthalimido-6,2',3',4'-tetra-O-acetyl-10,6'-dideoxyaucubin 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以40%的产率得到10-amino-6'-N-acetylamino-10,6'-dideoxyaucubin
  参考文献：
  名称：

  Regioselective and Stereospecific Amination of Iridoids:  Conversion of Aucubin into Aminoside Antibiotic Analogues

  摘要：

  Treatment of aucubin (1) with tert-butyldimethylsilyl chloride under alkaline conditions permitted regioselective silylation of either the primary hydroxyl groups at C-9 and C-6' or both primary hydroxyl groups and the secondary allylic hydroxyl group at C-6. Acetylation with acetic anhydride, followed by selective removal of the silyl groups and Mitsunobu reaction involving phthalimide as nitrogen donor, gave a stereospecific entry to aminoside antibiotic analogues: 10,6'-diamino-10,6'-dideoxyaucubin (16) and (6R)-6,10,6'-triamino-6,10,6'-trideoxyaucubin (17).

  DOI：

  10.1021/np060368v
• 作为产物：
  描述：

  6,2',3',4'-tetra-O-acetylaucubin 、 邻苯二甲酸亚胺 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.75h， 以75%的产率得到10,6'-diphthalimido-6,2',3',4'-tetra-O-acetyl-10,6'-dideoxyaucubin
  参考文献：
  名称：

  Regioselective and Stereospecific Amination of Iridoids:  Conversion of Aucubin into Aminoside Antibiotic Analogues

  摘要：

  Treatment of aucubin (1) with tert-butyldimethylsilyl chloride under alkaline conditions permitted regioselective silylation of either the primary hydroxyl groups at C-9 and C-6' or both primary hydroxyl groups and the secondary allylic hydroxyl group at C-6. Acetylation with acetic anhydride, followed by selective removal of the silyl groups and Mitsunobu reaction involving phthalimide as nitrogen donor, gave a stereospecific entry to aminoside antibiotic analogues: 10,6'-diamino-10,6'-dideoxyaucubin (16) and (6R)-6,10,6'-triamino-6,10,6'-trideoxyaucubin (17).

  DOI：

  10.1021/np060368v