(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(7-methoxyimidazo[4,5-b]pyridin-3-yl)oxolan-3-ol | 1326741-21-2

• 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: (2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(7-methoxyimidazo[4,5-b]pyridin-3-yl)oxolan-3-ol
• CAS: 1326741-21-2
• 化学式: C₃₃H₃₃N₃O₆
• 分子量: 567.642
• InChiKey: RNKWAYLBFHDQJK-GNSPLJBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(7-methoxyimidazo[4,5-b]pyridin-3-yl)oxolan-3-ol 、 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 30.0h， 以55%的产率得到3-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(7-methoxyimidazo[4,5-b]pyridin-3-yl)oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
  参考文献：
  名称：

  Efficient Synthesis of 1-Deaza-6-methoxypurine-N9-β-2′-deoxyribonucleoside and Related DNA Building Blocks

  摘要：

  An improved synthesis of the 2'-deoxyribonucleoside containing 1-deaza-6-methoxypurine as artificial nucleobase is described. By optimizing the conditions for the deprotection of p-toluoyl-protected 1-deaza-6-nitropurine 2'-deoxyribonucleoside, the isolated yield of the title compound could be increased from 15% to 90%. In addition, the synthesis and characterization of the corresponding 5'-(4,4'-dimethoxytrityl) (DMT) protected phosphoramidite, a potentially useful building block for the synthesis of artificial oligonucleotides, is reported. The title compound offers interesting hydrogen bond donor and metal-binding properties for its application in metal-mediated base pairs.

  DOI：

  10.1080/00397911.2010.505704
• 作为产物：
  描述：

  7-nitro-3-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-ribofuranosyl)imidazo[4,5-b]pyridine 在 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 5.0h， 生成 (2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(7-methoxyimidazo[4,5-b]pyridin-3-yl)oxolan-3-ol
  参考文献：
  名称：

  Efficient Synthesis of 1-Deaza-6-methoxypurine-N9-β-2′-deoxyribonucleoside and Related DNA Building Blocks

  摘要：

  An improved synthesis of the 2'-deoxyribonucleoside containing 1-deaza-6-methoxypurine as artificial nucleobase is described. By optimizing the conditions for the deprotection of p-toluoyl-protected 1-deaza-6-nitropurine 2'-deoxyribonucleoside, the isolated yield of the title compound could be increased from 15% to 90%. In addition, the synthesis and characterization of the corresponding 5'-(4,4'-dimethoxytrityl) (DMT) protected phosphoramidite, a potentially useful building block for the synthesis of artificial oligonucleotides, is reported. The title compound offers interesting hydrogen bond donor and metal-binding properties for its application in metal-mediated base pairs.

  DOI：

  10.1080/00397911.2010.505704

文献信息

• Efficient Synthesis of 1-Deaza-6-methoxypurine-N9-<font>β</font>-2′-deoxyribonucleoside and Related DNA Building Blocks
  作者：Dominik A. Megger、Jens Müller

  DOI：10.1080/00397911.2010.505704

  日期：2011.9.1

  An improved synthesis of the 2'-deoxyribonucleoside containing 1-deaza-6-methoxypurine as artificial nucleobase is described. By optimizing the conditions for the deprotection of p-toluoyl-protected 1-deaza-6-nitropurine 2'-deoxyribonucleoside, the isolated yield of the title compound could be increased from 15% to 90%. In addition, the synthesis and characterization of the corresponding 5'-(4,4'-dimethoxytrityl) (DMT) protected phosphoramidite, a potentially useful building block for the synthesis of artificial oligonucleotides, is reported. The title compound offers interesting hydrogen bond donor and metal-binding properties for its application in metal-mediated base pairs.