[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[4-(2-trimethylsilylethynyl)phenoxy]oxan-2-yl]methyl acetate | 694520-16-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[4-(2-trimethylsilylethynyl)phenoxy]oxan-2-yl]methyl acetate
• CAS: 694520-16-6
• 化学式: C₂₅H₃₂O₁₀Si
• 分子量: 520.609
• InChiKey: SIURQAMWVBEWEE-VAFBSOEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[4-(2-trimethylsilylethynyl)phenoxy]oxan-2-yl]methyl acetate 在 四丁基氟化铵 、 copper diacetate 、 溶剂黄146 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 50.0h， 生成 bis[4-(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：

  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 36.0h， 生成 [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[4-(2-trimethylsilylethynyl)phenoxy]oxan-2-yl]methyl acetate
  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