2-ethynylphenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside | 871311-12-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-ethynylphenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(2-ethynylphenoxy)oxan-2-yl]methyl acetate
• CAS: 871311-12-5
• 化学式: C₂₂H₂₄O₁₀
• 分子量: 448.427
• InChiKey: WCRPCYXFJFFICT-AANPDWTMSA-N

物化性质

• 沸点：
  527.2±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-ethynylphenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 copper diacetate 作用下， 以 吡啶 为溶剂， 反应 24.0h， 以63%的产率得到bis[2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]buta-1,3-diyne
  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：

  2-iodophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 四(三苯基膦)钯 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 三乙胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-ethynylphenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
  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