(2R,3R,4S,5S)-2-(2-chloro-6-(dimethylamino)-9H-purin-9-yl)-5-(chloromethyl)tetrahydrofuran-3,4-diol | 196497-01-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: (2R,3R,4S,5S)-2-(2-chloro-6-(dimethylamino)-9H-purin-9-yl)-5-(chloromethyl)tetrahydrofuran-3,4-diol
• 英文别名: (2R,3R,4S,5S)-2-[2-chloro-6-(dimethylamino)purin-9-yl]-5-(chloromethyl)oxolane-3,4-diol
• CAS: 196497-01-5
• 化学式: C₁₂H₁₅Cl₂N₅O₃
• 分子量: 348.189
• InChiKey: VMKWMIGBMOARPV-IOSLPCCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  96.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  DL-高半胱氨酸 、 (2R,3R,4S,5S)-2-(2-chloro-6-(dimethylamino)-9H-purin-9-yl)-5-(chloromethyl)tetrahydrofuran-3,4-diol 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 3.5h， 以27%的产率得到2-amino-4-(((2S,3S,4R)-5-(2-chloro-6-(dimethylmino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methylthio)butanoic acid
  参考文献：
  名称：

  An efficient synthesis of base-substituted analogues of S-adenosyl-dl-homocysteine

  摘要：

  An efficient method for the preparation of base-substituted S-adenosyl-DL-homocysteine analogues as well as of 2-chloro-N-6-alkylated S-adenosyl-DL-homocysteine analogues is described. The method uses a convergent strategy that employs a common intermediate late in the overall synthesis and allows small libraries of SAH analogues to be prepared in a relatively short period of time. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.076
• 作为产物：
  描述：

  2-chloro-N⁶,N⁶-dimethyladenosine 在 吡啶 、 氯化亚砜 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以79%的产率得到(2R,3R,4S,5S)-2-(2-chloro-6-(dimethylamino)-9H-purin-9-yl)-5-(chloromethyl)tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  An efficient synthesis of base-substituted analogues of S-adenosyl-dl-homocysteine

  摘要：

  An efficient method for the preparation of base-substituted S-adenosyl-DL-homocysteine analogues as well as of 2-chloro-N-6-alkylated S-adenosyl-DL-homocysteine analogues is described. The method uses a convergent strategy that employs a common intermediate late in the overall synthesis and allows small libraries of SAH analogues to be prepared in a relatively short period of time. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.076

文献信息

• An efficient synthesis of base-substituted analogues of S-adenosyl-dl-homocysteine
  作者：David B. Llewellyn、Amal Wahhab

  DOI：10.1016/j.tetlet.2009.04.076

  日期：2009.7

  An efficient method for the preparation of base-substituted S-adenosyl-DL-homocysteine analogues as well as of 2-chloro-N-6-alkylated S-adenosyl-DL-homocysteine analogues is described. The method uses a convergent strategy that employs a common intermediate late in the overall synthesis and allows small libraries of SAH analogues to be prepared in a relatively short period of time. (C) 2009 Elsevier Ltd. All rights reserved.