((2R,3S,5R)-3-acetoxy-5-(2,4-dioxo-5-((trimethylsilyl)ethynyl-1,2-13C2)-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl acetate | 1610530-36-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: ((2R,3S,5R)-3-acetoxy-5-(2,4-dioxo-5-((trimethylsilyl)ethynyl-1,2-13C2)-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl acetate
• CAS: 1610530-36-3
• 化学式: C₁₈H₂₄N₂O₇Si
• 分子量: 410.461
• InChiKey: QPBVAPCEENIYRQ-RCYQPOOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.55
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  116.69
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ((2R,3S,5R)-3-acetoxy-5-(2,4-dioxo-5-((trimethylsilyl)ethynyl-1,2-13C2)-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl acetate 在 zhang's catalyst 、 四丁基氟化铵 、 水 、 potassium carbonate 作用下， 以 甲醇 、 四氯化碳 为溶剂， 反应 15.0h， 生成 5-(ethynyl-13C)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Multicolor Live-Cell Chemical Imaging by Isotopically Edited Alkyne Vibrational Palette

  摘要：

  Vibrational imaging such as Raman microscopy is a powerful technique for visualizing a variety of molecules in live cells and tissues with chemical contrast. Going beyond the conventional label-free modality, recent advance of coupling alkyne vibrational tags with stimulated Raman scattering microscopy paves the way for imaging a wide spectrum of alkyne-labeled small biomolecules with superb sensitivity, specificity, resolution, biocompatibility, and minimal perturbation. Unfortunately, the currently available alkyne tag only processes a single vibrational "color", which prohibits multiplex chemical imaging of small molecules in a way that is being routinely practiced in fluorescence microscopy. Herein we develop a three-color vibrational palette of alkyne tags using a C-13-based isotopic editing strategy. We first synthesized C-13 isotopologues of EdU, a DNA metabolic reporter, by using the newly developed alkyne cross-metathesis reaction. Consistent with theoretical predictions, the mono-C-13 (C-13 C-12) and bis-C-13 (C-13 C-13) labeled alkyne isotopologues display Raman peaks that are red-shifted and spectrally resolved from the originally unlabeled (C-12 C-12) alkynyl probe. We further demonstrated three-color chemical imaging of nascent DNA, RNA, and newly uptaken fatty-acid in live mammalian cells with a simultaneous treatment of three different isotopically edited alkynyl metabolic reporters. The alkyne vibrational palette presented here thus opens up multicolor imaging of small biomolecules, enlightening a new dimension of chemical imaging.

  DOI：

  10.1021/ja502706q
• 作为产物：
  描述：

  碘苷 在 吡啶 、 copper(l) iodide 、 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 反应 19.0h， 生成 ((2R,3S,5R)-3-acetoxy-5-(2,4-dioxo-5-((trimethylsilyl)ethynyl-1,2-13C2)-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl acetate
  参考文献：
  名称：

  [EN] DEVICES, COMPOSITIONS AND METHODS FOR IMAGING WITH RAMAN SCATTERING
  [FR] DISPOSITIFS, COMPOSITIONS ET PROCÉDÉS POUR UNE IMAGERIE À DIFFUSION RAMAN

  摘要：

  公开号：

  WO2014205074A3