28-O-allyl-oleanate-3-yl 2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl-(1->2)-3,4-di-O-acetyl-α-L-arabinopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 562834-51-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 28-O-allyl-oleanate-3-yl 2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl-(1->2)-3,4-di-O-acetyl-α-L-arabinopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS: 562834-51-9
• 化学式: C₈₆H₁₀₁NO₂₄
• 分子量: 1532.74
• InChiKey: LCSHVBAHHANSEQ-BDUJUZLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.81
• 重原子数：
  111.0
• 可旋转键数：
  21.0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  303.16
• 氢给体数：
  0.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  28-O-allyl-oleanate-3-yl 2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl-(1->2)-3,4-di-O-acetyl-α-L-arabinopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Synthesis of a typical N-acetylglucosamine-containing saponin, oleanolic acid 3-yl α-l-arabinopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→6)-2-acetamido-2-deoxy-β-d-glucopyranoside

  摘要：

  Oleanolic acid 3-yl alpha-L-arabinopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl-(1 --> 6)-2-acetamido-2-deoxy-beta-D-glucopyranoside, a cytotoxic saponin isolated from Acacia tenuifolia and Albizia subdimidiata with a typical structure of the N-acetylglucosamine-containing plant saponins, was synthesized. The synthesis adopted a stepwise glycosylation fashion employing glycosyl trifluoroacetimidates 5 and 9 and thioglycoside 12 as donors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00047-8
• 作为产物：
  描述：

  2,3,4-tri-O-benzoyl-D-xylopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate 、 28-O-allyl-oleanate-3-yl 3,4-di-O-acetyl-α-L-arabinopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 Angstroem MS 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到28-O-allyl-oleanate-3-yl 2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl-(1->2)-3,4-di-O-acetyl-α-L-arabinopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a typical N-acetylglucosamine-containing saponin, oleanolic acid 3-yl α-l-arabinopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→6)-2-acetamido-2-deoxy-β-d-glucopyranoside

  摘要：

  Oleanolic acid 3-yl alpha-L-arabinopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl-(1 --> 6)-2-acetamido-2-deoxy-beta-D-glucopyranoside, a cytotoxic saponin isolated from Acacia tenuifolia and Albizia subdimidiata with a typical structure of the N-acetylglucosamine-containing plant saponins, was synthesized. The synthesis adopted a stepwise glycosylation fashion employing glycosyl trifluoroacetimidates 5 and 9 and thioglycoside 12 as donors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00047-8