1,2-bis[3-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)prop-1-ynyl]benzene | 1318797-51-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1,2-bis[3-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)prop-1-ynyl]benzene
• CAS: 1318797-51-1
• 化学式: C₄₀H₄₆O₂₀
• 分子量: 846.793
• InChiKey: HJXLQKIQVAQJRV-VTSLZQOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  60.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  247.32
• 氢给体数：
  0.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  1,2-bis[3-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)prop-1-ynyl]benzene 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以100%的产率得到1,2-bis[3-(α-D-mannopyranosyloxy)prop-1-ynyl]benzene
  参考文献：
  名称：

  Synthesis of a small library of bivalent α-d-mannopyranosides for lectin cross-linking

  摘要：

  A small library of bivalent alpha-D-mannopyranosides having rigid linkers was constructed in order to evaluate the effects of inter-saccharide distances upon multivalent binding interactions with plant and bacterial lectins. To this end, iodoaryl and propargyl alpha-D-mannopyranosides were synthesized and the former treated with TMS-acetylene under palladium chemistry to provide their corresponding ethynylaryl derivatives. A library of 15 dimeric members was then obtained using Lewis acid catalyzed glycosidation, aryl-aryl homocoupling, transition metal catalyzed Sonogashira cross-coupling reactions, and oxidative Glaser homocoupling. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.03.041
• 作为产物：
  描述：

  Α-D-五乙酸甘露糖酯 在 四(三苯基膦)钯 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 三乙胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 1,2-bis[3-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)prop-1-ynyl]benzene
  参考文献：
  名称：

  Synthesis of a small library of bivalent α-d-mannopyranosides for lectin cross-linking

  摘要：

  A small library of bivalent alpha-D-mannopyranosides having rigid linkers was constructed in order to evaluate the effects of inter-saccharide distances upon multivalent binding interactions with plant and bacterial lectins. To this end, iodoaryl and propargyl alpha-D-mannopyranosides were synthesized and the former treated with TMS-acetylene under palladium chemistry to provide their corresponding ethynylaryl derivatives. A library of 15 dimeric members was then obtained using Lewis acid catalyzed glycosidation, aryl-aryl homocoupling, transition metal catalyzed Sonogashira cross-coupling reactions, and oxidative Glaser homocoupling. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.03.041