(2S,3S,4R,5R)-3,4-diacetoxy-5-(2-amino-8-methoxy-6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-2-carboxylic acid | 1560688-72-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: (2S,3S,4R,5R)-3,4-diacetoxy-5-(2-amino-8-methoxy-6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-2-carboxylic acid
• CAS: 1560688-72-3
• 化学式: C₁₅H₁₇N₅O₉
• 分子量: 411.328
• InChiKey: SLKSECHPJZKMFX-KIKITERTSA-N

物化性质

• 沸点：
  696.6±65.0 °C(predicted)
• 密度：
  1.87±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.44
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  197.95
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N-{2-[2-(2-aminoethoxy)ethoxy]ethyl}acrylamide 、 (2S,3S,4R,5R)-3,4-diacetoxy-5-(2-amino-8-methoxy-6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-2-carboxylic acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以80%的产率得到[(2S,3S,4R,5R)-4-acetyloxy-5-(2-amino-8-methoxy-6-oxo-1H-purin-9-yl)-2-[2-[2-[2-(prop-2-enoylamino)ethoxy]ethoxy]ethylcarbamoyl]oxolan-3-yl] acetate
  参考文献：
  名称：

  Enhancing the Mechanical Properties of Guanosine-Based Supramolecular Hydrogels with Guanosine-Containing Polymers

  摘要：

  We demonstrate that multivalent, polymeric 8-methoxyguanosine derivatives based on poly(dimethylacrylamide) can enhance the mechanical properties of the low molecular weight hydrogelator 8-methoxy-2',3',5'-tri-O-acetylguanosine at biologically relevant salt concentrations. It is proposed that these nongelling polymeric derivatives, under the conditions studied, can result in a significant enhancement of these supramolecular gels (e.g., for gels containing 1 wt % gelator G' can be increased from ca. 2000 Pa with no additive to 80 000 Pa) by acting as supramolecular cross-linking units. Two competing mechanisms appear to play a role in these cogels. At low polymer concentrations the guanosine-containing polymers tend to act more as solubilizing agents for the gelator, thus weakening the gels, while at high guanosine-containing polymer concentrations the gels show a marked enhancement in mechanical properties consistent with them acting as supramolecular cross-linking agents. As such, the thermomechanical properties of these cogels depend on both the polymer:low molecular weight gelator ratio and the number of 8-methoxyguanosine repeat units present in the polymer additive. Thus, these polymeric guanosine-based additives impart the ability to tailor both the modulus and shear sensitivity of the gels. For example, cogels with a modulus ranging between ca. 95 and 80 000 Pa can be obtained through judicious selection of the type and amount of polymer additive.

  DOI：

  10.1021/ma402618z
• 作为产物：
  描述：

  2',3'-O-异丙亚基鸟苷 在 盐酸 、 4-二甲氨基吡啶 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 水 、 溴 、 碳酸氢钠 、 三乙胺 作用下， 以 甲醇 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 27.0h， 生成 (2S,3S,4R,5R)-3,4-diacetoxy-5-(2-amino-8-methoxy-6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-2-carboxylic acid
  参考文献：
  名称：

  Enhancing the Mechanical Properties of Guanosine-Based Supramolecular Hydrogels with Guanosine-Containing Polymers

  摘要：

  We demonstrate that multivalent, polymeric 8-methoxyguanosine derivatives based on poly(dimethylacrylamide) can enhance the mechanical properties of the low molecular weight hydrogelator 8-methoxy-2',3',5'-tri-O-acetylguanosine at biologically relevant salt concentrations. It is proposed that these nongelling polymeric derivatives, under the conditions studied, can result in a significant enhancement of these supramolecular gels (e.g., for gels containing 1 wt % gelator G' can be increased from ca. 2000 Pa with no additive to 80 000 Pa) by acting as supramolecular cross-linking units. Two competing mechanisms appear to play a role in these cogels. At low polymer concentrations the guanosine-containing polymers tend to act more as solubilizing agents for the gelator, thus weakening the gels, while at high guanosine-containing polymer concentrations the gels show a marked enhancement in mechanical properties consistent with them acting as supramolecular cross-linking agents. As such, the thermomechanical properties of these cogels depend on both the polymer:low molecular weight gelator ratio and the number of 8-methoxyguanosine repeat units present in the polymer additive. Thus, these polymeric guanosine-based additives impart the ability to tailor both the modulus and shear sensitivity of the gels. For example, cogels with a modulus ranging between ca. 95 and 80 000 Pa can be obtained through judicious selection of the type and amount of polymer additive.

  DOI：

  10.1021/ma402618z