2-(2-deoxy-β-D-erythro-pentofuranosyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6-diamine | 455886-17-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 2-(2-deoxy-β-D-erythro-pentofuranosyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6-diamine
• 英文别名: (2R,3S,5R)-5-(4,6-diaminopyrazolo[3,4-d]pyrimidin-2-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 455886-17-6
• 化学式: C₁₀H₁₄N₆O₃
• 分子量: 266.26
• InChiKey: GLEPNGUWCTUFPP-RRKCRQDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  145
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(2-deoxy-β-D-erythro-pentofuranosyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6-diamine 在 吡啶 、 三甲基氯硅烷 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.75h， 生成 2-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-N⁴,N⁶,N⁶-triisobutyryl-2H-pyrazolo[3,4-d]pyrimidine-4,6-diamine 3'-(2-cyanoethyl diisopropylphosphoramidite)
  参考文献：
  名称：

  Base Pairing of 8-Aza-7-deazapurine-2,6-diamine Linked via the N(8)-Position to the DNA Backbone: Universal Base-Pairing Properties and Formation of Highly Stable Duplexes when Alternating with dT

  摘要：

  The unusually N-8-glycosylated pyrazolo[3.4-d]pyrimidine-4.6-diamine 2'-deoxyribonucleoside (3) was synthesized and converted to the phosphoramidite 11. Oligonucleotides were prepared by solid-phase synthesis. and the base pairing Of compound 3 was Studied. In non-self-complementary duplexes containing compound 3, base pairs arc formed that show located opposite to the four canonical DNA constituents, strong ambiguous pairing properties. The self-complementary duplex d(3-T)(6) (34(.)34) is significantly more stable than d(A-T)(6).

  DOI：

  10.1002/1522-2675(200205)85:5<1340::aid-hlca1340>3.0.co;2-h
• 作为产物：
  描述：

  2-(2-deoxy-β-D-erythro-pentofuranosyl)-4-isopropoxy-2H-pyrazolo[3,4-d]pyrimidin-6-amine 在 氨 作用下， 以 水 为溶剂， 反应 96.0h， 以86%的产率得到2-(2-deoxy-β-D-erythro-pentofuranosyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6-diamine
  参考文献：
  名称：

  Base Pairing of 8-Aza-7-deazapurine-2,6-diamine Linked via the N(8)-Position to the DNA Backbone: Universal Base-Pairing Properties and Formation of Highly Stable Duplexes when Alternating with dT

  摘要：

  The unusually N-8-glycosylated pyrazolo[3.4-d]pyrimidine-4.6-diamine 2'-deoxyribonucleoside (3) was synthesized and converted to the phosphoramidite 11. Oligonucleotides were prepared by solid-phase synthesis. and the base pairing Of compound 3 was Studied. In non-self-complementary duplexes containing compound 3, base pairs arc formed that show located opposite to the four canonical DNA constituents, strong ambiguous pairing properties. The self-complementary duplex d(3-T)(6) (34(.)34) is significantly more stable than d(A-T)(6).

  DOI：

  10.1002/1522-2675(200205)85:5<1340::aid-hlca1340>3.0.co;2-h