1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-phenylsulfanyl-1H-pyrimidine-2,4-dione | 212075-44-0

• 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,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-phenylsulfanyl-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-5-phenylsulfanylpyrimidine-2,4-dione
• CAS: 212075-44-0
• 化学式: C₃₆H₃₄N₂O₇S
• 分子量: 638.741
• InChiKey: WDLBQCBEODVIBE-RKKDRKJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-phenylsulfanyl-1H-pyrimidine-2,4-dione 、 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 0.25h， 生成 Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,4-dioxo-5-phenylsulfanyl-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Facile Photocyclization Chemistry of 5-Phenylthio-2‘-deoxyuridine in Duplex DNA

  摘要：

  We report here the synthesis of 5-phenylthio-2 '-deoxyuridine (d(PhS)U), its incorporation into oligodeoxynucleotides (ODNs), and its photocyclization chemistry. Irradiation of dinucleoside monophosphate d((PhS)UG) and d(PhS)U-bearing duplex ODNs with 254 nm light results in the facile formation of a cyclic product where the C6 of uracil is covalently bonded to the C2 of the phenyl ring. The chemistry reported here may serve as the basis for the efficient preparation of a new class of duplex DNA with an extended pi system.

  DOI：

  10.1021/ol060659v
• 作为产物：
  描述：

  溴脲苷 在 吡啶 、 4-二甲氨基吡啶 、 TEA 、 sodium 作用下， 以 二甲基亚砜 为溶剂， 反应 23.0h， 生成 1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-phenylsulfanyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Facile Photocyclization Chemistry of 5-Phenylthio-2‘-deoxyuridine in Duplex DNA

  摘要：

  We report here the synthesis of 5-phenylthio-2 '-deoxyuridine (d(PhS)U), its incorporation into oligodeoxynucleotides (ODNs), and its photocyclization chemistry. Irradiation of dinucleoside monophosphate d((PhS)UG) and d(PhS)U-bearing duplex ODNs with 254 nm light results in the facile formation of a cyclic product where the C6 of uracil is covalently bonded to the C2 of the phenyl ring. The chemistry reported here may serve as the basis for the efficient preparation of a new class of duplex DNA with an extended pi system.

  DOI：

  10.1021/ol060659v