3-cyano-1-(2-deoxy-β-D-erythro-pentofuranosyl)-6-{[(dimethylamino)methylidene]amino}-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one | 252761-86-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 3-cyano-1-(2-deoxy-β-D-erythro-pentofuranosyl)-6-{[(dimethylamino)methylidene]amino}-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
• 英文别名: N'-[3-cyano-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-oxo-5H-pyrazolo[3,4-d]pyrimidin-6-yl]-N,N-dimethylmethanimidamide
• CAS: 252761-86-7
• 化学式: C₁₄H₁₇N₇O₄
• 分子量: 347.333
• InChiKey: WXBOYDKPEMHYSZ-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  148
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-cyano-1-(2-deoxy-β-D-erythro-pentofuranosyl)-6-{[(dimethylamino)methylidene]amino}-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.03h， 生成 3-cyano-1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-1,5-dihydro-6-{[(dimethylamino)methylidene]amino}-4H-pyrazolo[3,4-d]pyrimidin-4-one 3'-(2-cyanoethyl diisopropylphosphoramidite)
  参考文献：
  名称：

  Oligonucleotides Containing Pyrazolo[3,4-d]pyrimidines: The Influence of 7-Substituted 8-Aza-7-deaza-2′-deoxyguanosines on the Duplex Structure and Stability

  摘要：

  Oligonucleotides containing 7-substituted 8-aza-7-deazaguanines (= 6-amino-1,5-dihydro-4H-pyrazolo[3.4-d]pyrimidin-4-ones) were prepared by automated solid-phase synthesis. A series of 7-alkynylated 8-aza-7-deaza-2'-deoxyguanosines (see 4a-d)were synthesized with the 7-iodonucleoside 3c as starting material and by the Pd-0/Cu-I-catalyzed cross-coupling reaction with various alkynes. Phosphoramidites were prepared from the 7-substituted 8-aza-7-deaza-2'-deoxyguanosine derivatives carrying halogeno, cyano, and hexynyl substituents. From the melting profiles of oligonucleotide duplexes. the T-m values as well as the thermodynamic data were determined. A significant duplex stabilization by the 7-substituents was observed for the DNA . DNA duplexes, but not in the case of DNA . RNA hybrids.

  DOI：

  10.1002/(sici)1522-2675(19991006)82:10<1640::aid-hlca1640>3.0.co;2-n
• 作为产物：
  描述：

  N,N-二甲基甲酰胺二甲基缩醛 、 6-amino-3-cyano-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 以 甲醇 为溶剂， 反应 2.0h， 以27%的产率得到3-cyano-1-(2-deoxy-β-D-erythro-pentofuranosyl)-6-{[(dimethylamino)methylidene]amino}-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
  参考文献：
  名称：

  Oligonucleotides Containing Pyrazolo[3,4-d]pyrimidines: The Influence of 7-Substituted 8-Aza-7-deaza-2′-deoxyguanosines on the Duplex Structure and Stability

  摘要：

  Oligonucleotides containing 7-substituted 8-aza-7-deazaguanines (= 6-amino-1,5-dihydro-4H-pyrazolo[3.4-d]pyrimidin-4-ones) were prepared by automated solid-phase synthesis. A series of 7-alkynylated 8-aza-7-deaza-2'-deoxyguanosines (see 4a-d)were synthesized with the 7-iodonucleoside 3c as starting material and by the Pd-0/Cu-I-catalyzed cross-coupling reaction with various alkynes. Phosphoramidites were prepared from the 7-substituted 8-aza-7-deaza-2'-deoxyguanosine derivatives carrying halogeno, cyano, and hexynyl substituents. From the melting profiles of oligonucleotide duplexes. the T-m values as well as the thermodynamic data were determined. A significant duplex stabilization by the 7-substituents was observed for the DNA . DNA duplexes, but not in the case of DNA . RNA hybrids.

  DOI：

  10.1002/(sici)1522-2675(19991006)82:10<1640::aid-hlca1640>3.0.co;2-n