(1S,2R,3S,4S)-3-(6-chloro-5-aminopyrimidin-4-yl)amino-1,4-bis(hydroxymethyl)cyclopentane-1,2-diol | 221897-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (1S,2R,3S,4S)-3-(6-chloro-5-aminopyrimidin-4-yl)amino-1,4-bis(hydroxymethyl)cyclopentane-1,2-diol
• 英文别名: (1S,2R,3S,4S)-3-[(5-amino-6-chloropyrimidin-4-yl)amino]-1,4-bis(hydroxymethyl)cyclopentane-1,2-diol
• CAS: 221897-04-7
• 化学式: C₁₁H₁₇ClN₄O₄
• 分子量: 304.733
• InChiKey: IANJATZSCFDZKW-DCWRLNLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  145
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  甲醇 、 原甲酸三乙酯 、 (1S,2R,3S,4S)-3-(6-chloro-5-aminopyrimidin-4-yl)amino-1,4-bis(hydroxymethyl)cyclopentane-1,2-diol 在 对甲苯磺酸 作用下， 生成 (1'S,2'R,3'S,4'S)-9-<1,4-bis(hydroxymethyl)-1,2-dihydroxycyclopent-3-yl>-6-methoxyadenine 、 (1'S,2'R,3'S,4'S)-9-<1,4-bis(hydroxymethyl)-1,2-dihydroxycyclopent-3-yl>-6-dimethylaminoadenine
  参考文献：
  名称：

  Chiral Carbocyclic Nucleosides from d-Glucose:  Enantiodivergent Synthesis and One-Pot Entry of Dimethylamino Functionality in the Purine Rings

  摘要：

  Cyclization of appropriately designed enose-nitrones derived from D-glucose, having nitrone at C-5 or C-l and allylic/homoallylic functionalities at C-3 of the sugar backbone, afforded polyhydroxylated aminocarbocycles which were subsequently used as the precursors for carbocyclic nucleoside analogues (11, 13, 16, 21, and 23). The enantiodirecting synthesis of both the enantiomeric pairs of nucleoside analogues 11 and 13, 21a and 23a, and 21c and 23c, has also been demonstrated by judiciously applying intramolecular nitrone cycloaddition (INC) reaction. An interesting observation was that in the cyclization reaction of pyrimidine ring to purine ring in DMF solvent, the substitution of C-6 chloro group with a dimethylamino functionality also occurred spontaneously under mild condition, though similar reactions are reported to occur at higher temperature. The hydrogen bonding between N-3 of the purine ring and an appropriate hydroxy substituent in the carbocycle seems to play a crucial role in this reaction.

  DOI：

  10.1021/jo981955r
• 作为产物：
  描述：

  (3aS,5S,6R,6aS)-1-benzyl-5-(hydroxymethyl)-5-phenylmethoxy-3a,4,6,6a-tetrahydro-3H-cyclopenta[c][1,2]oxazol-6-ol 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 、 环己烯 、 正丁醇 为溶剂， 生成 (1S,2R,3S,4S)-3-(6-chloro-5-aminopyrimidin-4-yl)amino-1,4-bis(hydroxymethyl)cyclopentane-1,2-diol
  参考文献：
  名称：

  Chiral Carbocyclic Nucleosides from d-Glucose:  Enantiodivergent Synthesis and One-Pot Entry of Dimethylamino Functionality in the Purine Rings

  摘要：

  Cyclization of appropriately designed enose-nitrones derived from D-glucose, having nitrone at C-5 or C-l and allylic/homoallylic functionalities at C-3 of the sugar backbone, afforded polyhydroxylated aminocarbocycles which were subsequently used as the precursors for carbocyclic nucleoside analogues (11, 13, 16, 21, and 23). The enantiodirecting synthesis of both the enantiomeric pairs of nucleoside analogues 11 and 13, 21a and 23a, and 21c and 23c, has also been demonstrated by judiciously applying intramolecular nitrone cycloaddition (INC) reaction. An interesting observation was that in the cyclization reaction of pyrimidine ring to purine ring in DMF solvent, the substitution of C-6 chloro group with a dimethylamino functionality also occurred spontaneously under mild condition, though similar reactions are reported to occur at higher temperature. The hydrogen bonding between N-3 of the purine ring and an appropriate hydroxy substituent in the carbocycle seems to play a crucial role in this reaction.

  DOI：

  10.1021/jo981955r