methyl (Z)-2-(6'-azido-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate | 295797-73-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (Z)-2-(6'-azido-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate
• CAS: 295797-73-8
• 化学式: C₂₂H₂₅N₃O₁₁
• 分子量: 507.454
• InChiKey: ANZUOTNADUDPTL-WNGNDNCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  192.65
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl (Z)-2-(6'-azido-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以84%的产率得到methyl (Z)-2-(6'-azido-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate
  参考文献：
  名称：

  Synthetic Probe Compounds for Bioorganic Studies of Nyctinasty, Based on the Leaf-opening Substance of Lespedeza cuneata G. Don

  摘要：

  In a previous paper, the syntheses of potassium galactolespedezate (1) and potassium galactoisolespedezate (2), artificial leaf-opening substances useful for bioorganic studies of nyctinasty were reported. The fluorescent probe compounds, fluorescence-labeled galactoisolespedezate (3) and iodo-one (4), designed on the basis of 1 and 2 were prepared. Especially, compound 3 was bioactive at 5x10(-5) M, one-fiftieth as strong as the natural leaf-opening substance. This fluorescent probe would be useful for bioorganic studies of nyctinasty. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00421-x
• 作为产物：
  描述：

  (Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid methyl ester 在 吡啶 、 sodium azide 、 15-冠醚-5 、 四丁基氟化铵 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (Z)-2-(6'-azido-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate
  参考文献：
  名称：

  Syntheses of fluorescence-labeled artificial leaf-opening substances, fluorescent probe compounds useful for bioorganic studies of nyctinasty

  摘要：

  In a previous paper, the syntheses of potassium galactolespedezate (1) and potassium galactoisolespedezate (2), artificial leaf-opening substances useful for bioorganic studies of nyctinasty were reported. The fluorescent probe compounds, fluorescence-labeled galactoisolespedezates (3, 10, 13), designed on the basis of 1 and 2, were prepared. In particular, compound 3 was bioactive at 5 X 10(-5) M, one-fiftieth as strong as the natural leaf-opening substance. This fluorescent probe would be useful for bioorganic studies of nyctinasty. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00394-4