4-(2,6-Dichloro-phenoxy)-1-{(2R,3R,4S,5S)-3-hydroxy-5-hydroxymethyl-4-[2-(4-methoxy-phenoxy)-ethyl]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidin-2-one | 174088-55-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2,6-Dichloro-phenoxy)-1-{(2R,3R,4S,5S)-3-hydroxy-5-hydroxymethyl-4-[2-(4-methoxy-phenoxy)-ethyl]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidin-2-one
• CAS: 174088-55-2
• 化学式: C₂₅H₂₆Cl₂N₂O₇
• 分子量: 537.397
• InChiKey: AUEVIGIZXWUHAJ-FGSUIDRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  112.27
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  4-(2,6-Dichloro-phenoxy)-1-{(2R,3R,4S,5S)-3-hydroxy-5-hydroxymethyl-4-[2-(4-methoxy-phenoxy)-ethyl]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidin-2-one 在 咪唑 、 ammonium cerium(IV) nitrate 、 sodium hydride 、 三乙胺 、 四甲基胍 、 4-硝基苯甲醛肟 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 19.5h， 生成 1-[(2R,4S,5S)-5-[2-[(2S,3R,4R,5R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-methoxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]ethylsulfanylmethyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of 2′-Substituted Sulfide-Linked Dinucleotides

  摘要：

  3'-Deoxy-3'-(2-mesyloxyethyl)ribofuranosylthymine derivative 3, and its 2'-methoxy (16) and 2'-deoxy (38) analogs were condensed with 5'-deoxy-5'-thiothymidine 4 and 17 or 2'-O-methyl-5'-deoxy-5'-thiouridine 34 and 37 to provide, after standard functional group transformations, thymidine-thymidine and uridine-thymidine dimers 9, 21, 43 and 47. Oxidation of model sulfide dimer 48 with oxone gave sulfone 49. It was not stable to 27% ammonia.

  DOI：

  10.1080/15257779508010717
• 作为产物：
  描述：

  [(2S,3R,4R,5R)-4-acetyloxy-5-[4-(2,6-dichlorophenoxy)-5-methyl-2-oxopyrimidin-1-yl]-3-[2-(4-methoxyphenoxy)ethyl]oxolan-2-yl]methyl acetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以91%的产率得到4-(2,6-Dichloro-phenoxy)-1-{(2R,3R,4S,5S)-3-hydroxy-5-hydroxymethyl-4-[2-(4-methoxy-phenoxy)-ethyl]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidin-2-one
  参考文献：
  名称：

  Synthesis of 2′-Substituted Sulfide-Linked Dinucleotides

  摘要：

  3'-Deoxy-3'-(2-mesyloxyethyl)ribofuranosylthymine derivative 3, and its 2'-methoxy (16) and 2'-deoxy (38) analogs were condensed with 5'-deoxy-5'-thiothymidine 4 and 17 or 2'-O-methyl-5'-deoxy-5'-thiouridine 34 and 37 to provide, after standard functional group transformations, thymidine-thymidine and uridine-thymidine dimers 9, 21, 43 and 47. Oxidation of model sulfide dimer 48 with oxone gave sulfone 49. It was not stable to 27% ammonia.

  DOI：

  10.1080/15257779508010717