6-[[(dimethylamino)methylidene]amino]-1-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythropentofuranosyl]-1,5-dihydro-3-ethynyl-4H-pyrazolo[3,4-d]pyrimidin-4-one | 1312701-73-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 6-[[(dimethylamino)methylidene]amino]-1-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythropentofuranosyl]-1,5-dihydro-3-ethynyl-4H-pyrazolo[3,4-d]pyrimidin-4-one
• CAS: 1312701-73-7
• 化学式: C₃₆H₃₆N₆O₆
• 分子量: 648.718
• InChiKey: IJAMQQZKTCCFTM-OJDZSJEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  48.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  136.32
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  6-[[(dimethylamino)methylidene]amino]-1-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythropentofuranosyl]-1,5-dihydro-3-ethynyl-4H-pyrazolo[3,4-d]pyrimidin-4-one 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以74%的产率得到6-[[(dimethylamino)methylidene]amino]-1-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythropentofuranosyl]-1,5-dihydro-3-ethynyl-4H-pyrazolo[3,4-d]pyrimidin-4-one 3'-[(2-cyanoethyl)-N,N-(diisopropyl)]phosphoramidite
  参考文献：
  名称：

  Stepwise “Click” Chemistry for the Template Independent Construction of a Broad Variety of Cross-Linked Oligonucleotides: Influence of Linker Length, Position, and Linking Number on DNA Duplex Stability

  摘要：

  Cross-linked DNA was constructed by a "stepwise click" reaction using a bis-azide. The reaction is performed in the absence of a template, and a monofunctionalized oligonucleotide bearing an azido-function is formed as intermediate. For this, an excess of the bis-azide has to be used compared to the alkynylated oligonucleotide. The cross-linking can be carried out with any alkynylated DNA having a terminal triple bond at any position of the oligonucleotide, independent of chain length or sequence with identical or nonidentical chains. Short and long linkers with terminal triple bonds were introduced in the 7-position of 8-aza-7-deaza-2'-deoxyguanosine, (1 or 2), and the outcome of the "stepwise" click and the "bis-click" reaction was compared. The cross linked DNAs form cross linked duplexes when hybridized with single stranded complementary oligonucleotides. The stability of these cross linked duplexes is as high as respective individual duplexes when they were ligated at terminal positions with linkers of sufficient length. The stability decreases when the linkers are incorporated at central positions. The highest duplex stability was reached when two complementary cross-linked oligonucleotides were hybridized.

  DOI：

  10.1021/jo2004988
• 作为产物：
  描述：

  6-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-3-iodo-4H-pyrazolo[3,4-d]pyrimidin-4-one 在 吡啶 、 甲醇 、 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.0h， 生成 6-[[(dimethylamino)methylidene]amino]-1-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythropentofuranosyl]-1,5-dihydro-3-ethynyl-4H-pyrazolo[3,4-d]pyrimidin-4-one
  参考文献：
  名称：

  Stepwise “Click” Chemistry for the Template Independent Construction of a Broad Variety of Cross-Linked Oligonucleotides: Influence of Linker Length, Position, and Linking Number on DNA Duplex Stability

  摘要：

  Cross-linked DNA was constructed by a "stepwise click" reaction using a bis-azide. The reaction is performed in the absence of a template, and a monofunctionalized oligonucleotide bearing an azido-function is formed as intermediate. For this, an excess of the bis-azide has to be used compared to the alkynylated oligonucleotide. The cross-linking can be carried out with any alkynylated DNA having a terminal triple bond at any position of the oligonucleotide, independent of chain length or sequence with identical or nonidentical chains. Short and long linkers with terminal triple bonds were introduced in the 7-position of 8-aza-7-deaza-2'-deoxyguanosine, (1 or 2), and the outcome of the "stepwise" click and the "bis-click" reaction was compared. The cross linked DNAs form cross linked duplexes when hybridized with single stranded complementary oligonucleotides. The stability of these cross linked duplexes is as high as respective individual duplexes when they were ligated at terminal positions with linkers of sufficient length. The stability decreases when the linkers are incorporated at central positions. The highest duplex stability was reached when two complementary cross-linked oligonucleotides were hybridized.

  DOI：

  10.1021/jo2004988