N3-benzoyl-2'-deoxy-2'-methylideneuridine | 156900-03-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N3-benzoyl-2'-deoxy-2'-methylideneuridine
• 英文别名: N³-benzoyl-2'-deoxy-2'-methylideneuridine
• CAS: 156900-03-7
• 化学式: C₁₇H₁₆N₂O₆
• 分子量: 344.324
• InChiKey: QSPYYQDRMYCGHE-IVMMDQJWSA-N

物化性质

• 沸点：
  567.9±60.0 °C(predicted)
• 密度：
  1.51±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.49
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  110.76
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N3-benzoyl-2'-deoxy-2'-methylideneuridine 在 吡啶 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 (3'R)-N³-benzoyl-2',3'-dideoxy-5'-O-dimethylhexylsilyl-3'-fluoro-2'-methylideneuridine
  参考文献：
  名称：

  Nucleosides and Nucleotides. 125. Synthesis and Biological Evaluation of 2′,3′-Dideoxy-3′-fluoro-2′-methylidene Pyrimidine Nucleosides

  摘要：

  Reaction of 2'-deoxy-2'-methylidene-5'-O-trityluridine (1) with diethylamino-sulfur trifluoride (DAST) in CH2Cl2 resulted in the formation of a mixture of (3'R)-2',3'-dideoxy-3'-fluoro-2'-methylidene derivative 3 and 2',3'-didehydro-2',3'-dideoxy-2'-fluoromethyl derivative 4 (3:4 = 1:1.5) in 65% yield. A similar treatment of 1-(2-deoxy-2-methylidene-5-O-trityl-beta-D-threo-pentofuranosyl)uracil (19) with DAST in CH2Cl2 afforded (3'S)-2',3'-dideoxy-3'-fluoro-2'-methylidene derivatives 20 and 4 in 38% and 17% yields respectively. Transformation of the uracil nucleosides 4, 12, and 20 into cytosines followed by deprotection furnished the corresponding cytidine derivatives 29, 18, and 25, respectively. The corresponding thymidine congener 27 was also synthesized in a similar manner. All of the newly synthesized nucleosides were evaluated for their inhibitory activities against HIV and for their antiproliferative activities against L1210 and KB cells.

  DOI：

  10.1080/15257779408013235
• 作为产物：
  描述：

  1-((6aR,8R,9aS)-2,2,4,4-tetraisopropyl-9-methylenetetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidine-2,4(1H,3H)-dione 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 38.0h， 生成 N3-benzoyl-2'-deoxy-2'-methylideneuridine
  参考文献：
  名称：

  Nucleosides and Nucleotides. 125. Synthesis and Biological Evaluation of 2′,3′-Dideoxy-3′-fluoro-2′-methylidene Pyrimidine Nucleosides

  摘要：

  Reaction of 2'-deoxy-2'-methylidene-5'-O-trityluridine (1) with diethylamino-sulfur trifluoride (DAST) in CH2Cl2 resulted in the formation of a mixture of (3'R)-2',3'-dideoxy-3'-fluoro-2'-methylidene derivative 3 and 2',3'-didehydro-2',3'-dideoxy-2'-fluoromethyl derivative 4 (3:4 = 1:1.5) in 65% yield. A similar treatment of 1-(2-deoxy-2-methylidene-5-O-trityl-beta-D-threo-pentofuranosyl)uracil (19) with DAST in CH2Cl2 afforded (3'S)-2',3'-dideoxy-3'-fluoro-2'-methylidene derivatives 20 and 4 in 38% and 17% yields respectively. Transformation of the uracil nucleosides 4, 12, and 20 into cytosines followed by deprotection furnished the corresponding cytidine derivatives 29, 18, and 25, respectively. The corresponding thymidine congener 27 was also synthesized in a similar manner. All of the newly synthesized nucleosides were evaluated for their inhibitory activities against HIV and for their antiproliferative activities against L1210 and KB cells.

  DOI：

  10.1080/15257779408013235