Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[9-(4-methoxy-2-methyl-phenyl)-6-oxo-6H-xanthen-3-yloxy]-tetrahydro-pyran-3-yl ester | 847978-23-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[9-(4-methoxy-2-methyl-phenyl)-6-oxo-6H-xanthen-3-yloxy]-tetrahydro-pyran-3-yl ester
• CAS: 847978-23-8
• 化学式: C₃₅H₃₄O₁₃
• 分子量: 662.647
• InChiKey: UGVADFMSTIVKEX-CYNLXDPFSA-N

物化性质

• 沸点：
  773.3±60.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  48.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  163.1
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[9-(4-methoxy-2-methyl-phenyl)-6-oxo-6H-xanthen-3-yloxy]-tetrahydro-pyran-3-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以85.4%的产率得到9-(4’-methoxy-2’-methylphenyl)-6-(β-D-galactopyranosyloxy)xanthen-3-one
  参考文献：
  名称：

  Evolution of Fluorescein as a Platform for Finely Tunable Fluorescence Probes

  摘要：

  Fluorescence imaging is the most powerful technique currently available for continuous observation of dynamic intracellular processes in living cells. Suitable fluorescence probes are naturally of critical importance for fluorescence imaging, but only a very limited range of biomolecules can currently be visualized because of the lack of flexible design strategies for fluorescence probes. At present, design is largely empirical. Here we show that the carboxylic group of traditional fluorescein dyes, formerly considered indispensable, has been replaced with other substituents, affording various kinds of new fluoresceins. Further, by breaking out of the traditional structure of fluorescein, we developed the first and totally rational design strategy for novel fluorescence probes based on a strict photochemical basis. The value of this approach is exemplified by its application to develop a novel, highly sensitive, and membrane-permeable fluorescence probe for beta-galactosidase, which is the most widely used reporter enzyme.

  DOI：

  10.1021/ja043919h
• 作为产物：
  描述：

  magnesium,1-methoxy-3-methylbenzene-4-ide,bromide 在 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[9-(4-methoxy-2-methyl-phenyl)-6-oxo-6H-xanthen-3-yloxy]-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Evolution of Fluorescein as a Platform for Finely Tunable Fluorescence Probes

  摘要：

  Fluorescence imaging is the most powerful technique currently available for continuous observation of dynamic intracellular processes in living cells. Suitable fluorescence probes are naturally of critical importance for fluorescence imaging, but only a very limited range of biomolecules can currently be visualized because of the lack of flexible design strategies for fluorescence probes. At present, design is largely empirical. Here we show that the carboxylic group of traditional fluorescein dyes, formerly considered indispensable, has been replaced with other substituents, affording various kinds of new fluoresceins. Further, by breaking out of the traditional structure of fluorescein, we developed the first and totally rational design strategy for novel fluorescence probes based on a strict photochemical basis. The value of this approach is exemplified by its application to develop a novel, highly sensitive, and membrane-permeable fluorescence probe for beta-galactosidase, which is the most widely used reporter enzyme.

  DOI：

  10.1021/ja043919h

文献信息

• Fluorescent probe
  申请人：——

  公开号：US07868147B2

  公开（公告）日：2011-01-11

  A fluorescent probe which is represented by the following formula (I): (wherein, R1 represents a monovalent substituent other than hydrogen atom, carboxy group, or sulfo group; R2 represents hydrogen atom, or a monovalent substituent; R3 and R4 each independently represents hydrogen atom or a halogen atom; and R5 represents a monovalent group which is cleaved by contact with a measuring object, provided that a combination of R1 and R2 is selected so that the oxidation potential of the benzene ring to which they bind makes (1) the compound represented by the formula (I) substantially no fluorescent before the cleavage, and (2) a compound after the cleavage, which is derived from the compound represented by the formula (I), substantially highly fluorescent after the cleavage).

  以下公式（I）代表的一种荧光探针： （其中，R1代表除氢原子、羧基或磺酸基以外的单价取代基；R2代表氢原子或单价取代基；R3和R4各自独立代表氢原子或卤素原子；R5代表通过与测量对象接触而被裂解的单价基团，前提是R1和R2的组合选择使得它们结合的苯环的氧化电位使得（1）在裂解前，由公式（I）表示的化合物基本上无荧光，并且（2）裂解后，从由公式（I）表示的化合物衍生出的化合物在裂解后基本上具有高度荧光）。