1-O-[3β-acetoxy-lup-20(29)-ene-28-oyl]-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->3)-[(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->6)]-2,4-di-O-acetyl-α-D-mannopyranosyl | 1030385-85-3

• 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: 1-O-[3β-acetoxy-lup-20(29)-ene-28-oyl]-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->3)-[(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->6)]-2,4-di-O-acetyl-α-D-mannopyranosyl
• 英文别名: 3β-O-acetyl-lup-20(29)-en-28-oic acid (2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->3)-[(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->6)]-2,4-di-O-acetyl-α-D-mannopyranosyl ester
• CAS: 1030385-85-3
• 化学式: C₁₁₀H₁₁₆O₂₉
• 分子量: 1902.11
• InChiKey: JSAUMOXOTGRATA-DULGFZQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.63
• 重原子数：
  139.0
• 可旋转键数：
  29.0
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  361.75
• 氢给体数：
  0.0
• 氢受体数：
  29.0

反应信息

• 作为反应物：
  描述：

  1-O-[3β-acetoxy-lup-20(29)-ene-28-oyl]-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->3)-[(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->6)]-2,4-di-O-acetyl-α-D-mannopyranosyl 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以100%的产率得到1-O-[3β-acetoxy-lup-20(29)-ene-28-oyl]-(α-D-mannopyranosyl)-(1->3)-[(α-D-mannopyranosyl)-(1->6)]-α-D-mannopyranosyl
  参考文献：
  名称：

  [EN] SACCHARIDE LUPANE DERIVATIVES, THEIR USE AND PHARMACEUTICAL COMPOSITIONS CONTAINING THESE DERIVATIVES
  [FR] DÉRIVÉS DE SACCHARIDE LUPANE, LEUR UTILISATION ET COMPOSITIONS PHARMACEUTIQUES CONTENANT CES DÉRIVÉS

  摘要：

  本发明涉及一般式(I)的糖苷鲁潘衍生物，其中R表示从氢，羟基，氨基，巯基，烷氧基，烷基和糖基组成的群体中独立选择的取代基，R'表示从氢，羟基，烷基，羧基，酰基和糖基组成的群体中独立选择的取代基，其中至少一个R和R'含有糖基。本发明的另一个目的是将这些化合物用作药物和生长调节剂。本发明还包括含有上述衍生物的制药组合物。

  公开号：

  WO2009094958A1
• 作为产物：
  描述：

  1-O-[3β-acetoxy-lup-20(29)-ene-28-oyl]-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->3)-[(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->6)]-α-D-mannopyranosyl 、 乙酸酐 在 吡啶 作用下， 以391 mg的产率得到1-O-[3β-acetoxy-lup-20(29)-ene-28-oyl]-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->3)-[(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->6)]-2,4-di-O-acetyl-α-D-mannopyranosyl
  参考文献：
  名称：

  Synthesis of lupane-type saponins bearing mannosyl and 3,6-branched trimannosyl residues and their evaluation as anticancer agents

  摘要：

  The saponins modified with mono- or trimannosyl residues can provide a convenient means of delivering drugs to certain human cells via interactions with mannose receptors. In the study reported therein, we developed a convenient approach for the synthesis of 3-O-mannoside and branched trimannoside derivatives of the saponin lupeol and of C-28 acyl esters of 3-O-acetylbetulinic acid bearing the same mannosyl entities. Lupeol and 3-O-acetyl-betulinic acid were mannosylated with tetra-O-benzoyl-or tetra-O-acetyl-alpha-D-mannopyranosyl trichloroacetimidates. De-esterification followed by regioselective dimannosylation of the unprotected monosaccharide derivatives with 2 equiv of tetra-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate selectively yielded O-3,O-6-linked trimannosides. The cytotoxic activity of selected lupane-type saponins (derivatives of lupeol, betulinic acid, and betulin) toward normal human fibroblasts and various cancer cell lines was also compared. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.02.011