20-bromoicosanyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 1374551-81-1

• 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: 20-bromoicosanyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(20-bromoicosoxy)oxan-2-yl]methyl acetate
• CAS: 1374551-81-1
• 化学式: C₃₄H₅₉BrO₁₀
• 分子量: 707.74
• InChiKey: ZKHPUECEQYSYJI-BGSSSCFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  45
• 可旋转键数：
  30
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  20-bromoicosanyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 copper(l) iodide 、 二(三叔丁基膦)钯 、 水 、 potassium carbonate 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 14.0h， 生成 (2R,3R,4S,5S,6R)-2-[20-[6-[2-[6-[2-[tert-butyl(dimethyl)silyl]ethynyl]-4-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]pyridin-2-yl]ethynyl]pyridin-2-yl]oxyicosoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  Concentration- and Time-Dependent Eccentric Changes in Circular Dichroism of Saccharide-Linked Ethynylpyridine Oligomer with Copper(II) Ions

  摘要：

  We studied the preparation and circular dichroism (CD) behavior of 2,6-pyridylene ethynylene octameric oligomer linked to a beta-D-glucoside moiety with a C20-alkylene chain. The addition of Cu(OTf)(2) salt led to a remarkable enhancement of the first CD band of the oligomer, and an unexpected concentration and time dependency were observed. For example, when 1.0 X 10(-3) M of Cu(OTf)(2) was added to a 1,2-dichloroethane solution of the oligomer (5.0 X 10(-4) M, unit concentration), the CD band appeared in the positive at first and gradually inverted into the negative with time.

  DOI：

  10.1021/jo300735j
• 作为产物：
  描述：

  20-溴-1-二十烷醇 、 β-D-葡萄糖五乙酸酯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 33.5h， 以22%的产率得到20-bromoicosanyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Concentration- and Time-Dependent Eccentric Changes in Circular Dichroism of Saccharide-Linked Ethynylpyridine Oligomer with Copper(II) Ions

  摘要：

  We studied the preparation and circular dichroism (CD) behavior of 2,6-pyridylene ethynylene octameric oligomer linked to a beta-D-glucoside moiety with a C20-alkylene chain. The addition of Cu(OTf)(2) salt led to a remarkable enhancement of the first CD band of the oligomer, and an unexpected concentration and time dependency were observed. For example, when 1.0 X 10(-3) M of Cu(OTf)(2) was added to a 1,2-dichloroethane solution of the oligomer (5.0 X 10(-4) M, unit concentration), the CD band appeared in the positive at first and gradually inverted into the negative with time.

  DOI：

  10.1021/jo300735j