9-<(2R,5S)-2H-5,6-dihydro-2-<(diisopropylphosphonyl)methoxy>-5-pyranyl>-guanine | 166769-23-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-<(2R,5S)-2H-5,6-dihydro-2-<(diisopropylphosphonyl)methoxy>-5-pyranyl>-guanine
• CAS: 166769-23-9
• 化学式: C₁₇H₂₆N₅O₆P
• 分子量: 427.397
• InChiKey: QVAGKZRWZNKUOX-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  143.84
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  9-<(2R,5S)-2H-5,6-dihydro-2-<(diisopropylphosphonyl)methoxy>-5-pyranyl>-guanine 在 palladium on activated charcoal 2,6-二甲基吡啶 、 ammonium hydroxide 、 三甲基溴硅烷 、 氢气 作用下， 以 乙醇 为溶剂， 反应 35.0h， 生成 9-<(2R,5S)-tetrahydro-2-(phosphonomethoxy)-5-pyranyl>guanine ammonium salt
  参考文献：
  名称：

  Stereocontrolled synthesis of phosphonate derivatives of tetrahydro- and dihydro-2H-pyranyl nucleosides: The selectivity of the Ferrier rearrangement

  摘要：

  Phosphonate derivatives of 2,5-cis substituted tetrahydro- and dihydro-2H-pyranyl nucleosides have been synthesized following a stereocontrolled approach. The key step in the synthetic pathway is the introduction of the phosphonomethoxy moiety on pentopyranosyl glycals through a Ferrier-type rearrangement, yielding the 1,4-trans phosphonomethyl glycosides as the major isomers. The heterocyclic base has then been incorporated following a Mitsunobu-type condensation reaction, to obtain the 2,5-cis-dihydro-2H-pyranyl nucleosides. The tetrahydropyranyl analogues have been prepared through hydrogenation of 2,5-cis-dihydro-2H-pyranyl nucleosides.

  DOI：

  10.1016/0957-4166(95)00108-2
• 作为产物：
  描述：

  (diisopropylphosphonyl)methyl 2,3-dideoxy-α-D-glycero-pent-2-eno pyranoside 在 氨 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 、 偶氮二甲酸二乙酯 、 三甲胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 5.5h， 生成 9-<(2R,5S)-2H-5,6-dihydro-2-<(diisopropylphosphonyl)methoxy>-5-pyranyl>-guanine
  参考文献：
  名称：

  Stereocontrolled synthesis of phosphonate derivatives of tetrahydro- and dihydro-2H-pyranyl nucleosides: The selectivity of the Ferrier rearrangement

  摘要：

  Phosphonate derivatives of 2,5-cis substituted tetrahydro- and dihydro-2H-pyranyl nucleosides have been synthesized following a stereocontrolled approach. The key step in the synthetic pathway is the introduction of the phosphonomethoxy moiety on pentopyranosyl glycals through a Ferrier-type rearrangement, yielding the 1,4-trans phosphonomethyl glycosides as the major isomers. The heterocyclic base has then been incorporated following a Mitsunobu-type condensation reaction, to obtain the 2,5-cis-dihydro-2H-pyranyl nucleosides. The tetrahydropyranyl analogues have been prepared through hydrogenation of 2,5-cis-dihydro-2H-pyranyl nucleosides.

  DOI：

  10.1016/0957-4166(95)00108-2