allyl 3-O-[2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl]oleanolate | 1185255-33-7

• 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: allyl 3-O-[2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl]oleanolate
• CAS: 1185255-33-7
• 化学式: C₇₁H₁₀₂O₂₈
• 分子量: 1403.57
• InChiKey: FHYJPTDSSDOZDZ-HVMHTVGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.06
• 重原子数：
  99.0
• 可旋转键数：
  22.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  344.68
• 氢给体数：
  0.0
• 氢受体数：
  28.0

反应信息

• 作为反应物：
  描述：

  allyl 3-O-[2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl]oleanolate 在 甲酸铵 、 palladium diacetate 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems

  摘要：

  Immunostimulatory saponin based colloidal antigen delivery systems show promise as adjuvants for subunit vaccines. For this reason, allyl oleanolate was glycosylated at the 3-position using trichloroacetimidate donors to give monodesmodic saponins following deprotection. Bisdesmodic saponins were synthesized by double glycosylation at the 3- and 28-positions of oleanolic acid. When formulated together with cholesterol and phospholipids, ring-like, helical and rod-like nanostructures were formed depending on the saponin concentrations used. As an indication of adjuvant activity, the ability of these formulations, and the saponins by themselves, to induce dendritic cell maturation was measured, but no significant activity was observed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.043
• 作为产物：
  描述：

  Man2Ac3Ac4Ac6Ac(a1-2)Man3Ac4Ac6Ac(a1-2)Man3Ac4Ac6Ac(a)-O-C(NH)CCl3 、 allyl oleanate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以70%的产率得到allyl 3-O-[2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl]oleanolate
  参考文献：
  名称：

  Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems

  摘要：

  Immunostimulatory saponin based colloidal antigen delivery systems show promise as adjuvants for subunit vaccines. For this reason, allyl oleanolate was glycosylated at the 3-position using trichloroacetimidate donors to give monodesmodic saponins following deprotection. Bisdesmodic saponins were synthesized by double glycosylation at the 3- and 28-positions of oleanolic acid. When formulated together with cholesterol and phospholipids, ring-like, helical and rod-like nanostructures were formed depending on the saponin concentrations used. As an indication of adjuvant activity, the ability of these formulations, and the saponins by themselves, to induce dendritic cell maturation was measured, but no significant activity was observed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.043