1,2-bis[3-(α-D-mannopyranosyloxy)prop-1-ynyl]benzene | 871311-20-5

• 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-(α-D-mannopyranosyloxy)prop-1-ynyl]benzene
• 英文别名: (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-[3-[2-[3-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyprop-1-ynyl]phenyl]prop-2-ynoxy]oxane-3,4,5-triol
• CAS: 871311-20-5
• 化学式: C₂₄H₃₀O₁₂
• 分子量: 510.495
• InChiKey: XKSISMZHEHCZNC-PUYHWVFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  199
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  propargyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 四(三苯基膦)钯 、 sodium methylate 作用下， 以 甲醇 、 三乙胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 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