(2S,4R)-4-[2-amino-6-(2-nitrophenoxy)-purin-9-yl]-2-(tert-butoxycarbonylmethoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | 876954-00-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (2S,4R)-4-[2-amino-6-(2-nitrophenoxy)-purin-9-yl]-2-(tert-butoxycarbonylmethoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS: 876954-00-6
• 化学式: C₂₇H₃₅N₇O₈
• 分子量: 585.617
• InChiKey: ATOWRPPJTDBEEA-SJORKVTESA-N

物化性质

• 沸点：
  750.5±70.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  42.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  187.06
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (2S,4R)-4-[2-amino-6-(2-nitrophenoxy)-purin-9-yl]-2-(tert-butoxycarbonylmethoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 、 异丁酰氯 在 吡啶 作用下， 以100%的产率得到(2S,4R)-2-(tert-butoxycarbonylmethoxymethyl)-4-[2-isobutyrylamino-6-(2-nitrophenoxy)-purin-9-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of pyrrolidine-based oxy-peptide nucleic acids carrying four types of nucleobases and their transport into cytoplasm

  摘要：

  We synthesized 16 pyrrolidine-based oxy-peptide nucleic acid (POPNA) monomers carrying four different nucleobases onto four different stereoisomers of pyrrolidine rings. Using these monomers, we prepared POPNA oligomers, which formed sequence-specific hybrids with DNAs. The oligomer configurations influenced the hybrid stability. The oligomers were not taken into CHO cells. However, they could enter the cell cytoplasm when mixed with the influenza virus hemagglutinin peptide-arginine heptamer conjugate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.056
• 作为产物：
  描述：

  (2S,4R)-4-(2-amino-6-chloro-purin-9-yl)-2-(tert-butoxycarbonylmethoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 、 硝苯酚 在 三乙烯二胺 、 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 以78%的产率得到(2S,4R)-4-[2-amino-6-(2-nitrophenoxy)-purin-9-yl]-2-(tert-butoxycarbonylmethoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of pyrrolidine-based oxy-peptide nucleic acids carrying four types of nucleobases and their transport into cytoplasm

  摘要：

  We synthesized 16 pyrrolidine-based oxy-peptide nucleic acid (POPNA) monomers carrying four different nucleobases onto four different stereoisomers of pyrrolidine rings. Using these monomers, we prepared POPNA oligomers, which formed sequence-specific hybrids with DNAs. The oligomer configurations influenced the hybrid stability. The oligomers were not taken into CHO cells. However, they could enter the cell cytoplasm when mixed with the influenza virus hemagglutinin peptide-arginine heptamer conjugate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.056