1-{(2R,3R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-1H-pyridin-2-one | 175911-23-6

• 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: 1-{(2R,3R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-1H-pyridin-2-one
• CAS: 175911-23-6
• 化学式: C₃₁H₃₁NO₇
• 分子量: 529.59
• InChiKey: YPDHEYGUCICRCV-PYYPWFDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  39.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  99.38
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-{(2R,3R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-1H-pyridin-2-one 在 吡啶 、 N-甲基咪唑 、 silver nitrate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-(2-oxo-2H-pyridin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Synthesis of pyridinone ribonucleoside 3′-O-phosphoramidites and their incorporation into oligoribonucleotides

  摘要：

  Protected pyridin-2- and pyridin-4-one ribonucleosides 3 and 9 were synthesized using a one-pot reaction of silylated bases with 1-O-acetyl-tri-O-benzoyl-beta-D-ribofuranose (2) in the presence of CF(3)SO(3)SiMe(3) The nucleosides were converted in 4 steps into 3'-O-phosphoramidites 7 and 11 which were incorporated into hammerhead ribozyme substrates using solid-phase phosphoramidite chemistry.

  DOI：

  10.1016/0960-894x(96)00030-3
• 作为产物：
  描述：

  1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2(1H)-pyridinone 在 吡啶 、 4-二甲氨基吡啶 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 1-{(2R,3R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-1H-pyridin-2-one
  参考文献：
  名称：

  Synthesis of pyridinone ribonucleoside 3′-O-phosphoramidites and their incorporation into oligoribonucleotides

  摘要：

  Protected pyridin-2- and pyridin-4-one ribonucleosides 3 and 9 were synthesized using a one-pot reaction of silylated bases with 1-O-acetyl-tri-O-benzoyl-beta-D-ribofuranose (2) in the presence of CF(3)SO(3)SiMe(3) The nucleosides were converted in 4 steps into 3'-O-phosphoramidites 7 and 11 which were incorporated into hammerhead ribozyme substrates using solid-phase phosphoramidite chemistry.

  DOI：

  10.1016/0960-894x(96)00030-3