3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate | 1225290-13-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate
• CAS: 1225290-13-0
• 化学式: C₅₈H₅₅Cl₃N₄O₂₆
• 分子量: 1330.44
• InChiKey: RARCGZQWKRYSRU-VIAOGTRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  91.0
• 可旋转键数：
  18.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  375.47
• 氢给体数：
  1.0
• 氢受体数：
  27.0

反应信息

• 作为反应物：
  描述：

  ursolic acid trityl ester 、 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成
  参考文献：
  名称：

  Synthesis and cytotoxic activity of the N-acetylglucosamine-bearing triterpenoid saponins

  摘要：

  Fourteen ursolic acid and oleanolic acid saponins with N-acetyl-beta-D-glucosamine, and (1 -> 4)-linked and (1 6)-linked N-acetyl-beta-D-glucosamine oligosaccharide residues were synthesized in a convergent manner. The structures of all compounds were confirmed by (1)H NMR and (13)C NMR spectroscopy and by mass spectrometry, and their cytotoxic activities were assayed in three cancer cell lines. Only oleanolic acid-3-yl beta-D-GluNAc showed significant cytotoxicity against HL-60 and BGC-823. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2010.01.002
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis and cytotoxic activity of the N-acetylglucosamine-bearing triterpenoid saponins

  摘要：

  Fourteen ursolic acid and oleanolic acid saponins with N-acetyl-beta-D-glucosamine, and (1 -> 4)-linked and (1 6)-linked N-acetyl-beta-D-glucosamine oligosaccharide residues were synthesized in a convergent manner. The structures of all compounds were confirmed by (1)H NMR and (13)C NMR spectroscopy and by mass spectrometry, and their cytotoxic activities were assayed in three cancer cell lines. Only oleanolic acid-3-yl beta-D-GluNAc showed significant cytotoxicity against HL-60 and BGC-823. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2010.01.002