1-O-acetyl-2,3,4,6-tetra-O-benzoyl-D-mammopyranose | 121523-93-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-O-acetyl-2,3,4,6-tetra-O-benzoyl-D-mammopyranose
• CAS: 121523-93-1
• 化学式: C₃₆H₃₀O₁₁
• 分子量: 638.628
• InChiKey: WLPLSHLSRSOLFV-HJXGLETNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  47.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  140.73
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  3β-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->3)-[(2,3,4,6-tera-O-benzoyl-α-D-mannopyranosyl)-(1->6)]-α-D-mannopyranosyl-lup-20(29)-ene 、 乙酸酐 在 吡啶 作用下， 以251 mg的产率得到3β-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->3)-[(2,3,4,6-tera-O-benzoyl-α-D-mannopyranosyl)-(1->6)]-2,4-di-O-acetyl-α-D-mannopyranosyl-lup-20(29)-ene
  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