(Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid methyl ester | 295797-77-2

• 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: (Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid methyl ester
• CAS: 295797-77-2
• 化学式: C₂₂H₃₄O₉Si
• 分子量: 470.592
• InChiKey: QJQWTWOFEMUPJF-WIYCRDOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  134.91
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-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， 反应 53.58h， 生成 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 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以86%的产率得到(Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid methyl ester
  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

文献信息

• Visualization of the Precise Structure Recognition of Leaf-opening Substance by Using Biologically Inactive Probe Compounds: Fluorescence Studies of Nyctinasty in Legumes 2
  作者：Takanori Sugimoto、Shosuke Yamamura、Minoru Ueda

  DOI：10.1246/cl.2002.1118

  日期：2002.11

  Intimate correlation between bioactivity and binding activity was shown using biologically active and inactive fluorescence-labeled probe compounds for nyctinasty. This results suggested the existence of a receptor which recognizes the aglycon of a leaf-opening substance on the motor cell.

  使用生物活性和非生物活性荧光标记探针化合物对夜光性进行了研究，结果表明生物活性和结合活性之间存在密切关联。研究结果表明，存在一种受体，能够识别运动细胞上叶片张开物质的糖苷。
• Syntheses of fluorescence-labeled artificial leaf-opening substances, fluorescent probe compounds useful for bioorganic studies of nyctinasty
  作者：Minoru Ueda、Yoshiyuki Sawai、Shosuke Yamamura

  DOI：10.1016/s0040-4039(00)00394-4

  日期：2000.4

  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.