N,N-4(ditert-butoxycarbonyl)-1-(2,3-O-isopropylidene-β-D-ribo-(5R)-hexofuranosyl)cytosine | 1454612-00-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N,N-4(ditert-butoxycarbonyl)-1-(2,3-O-isopropylidene-β-D-ribo-(5R)-hexofuranosyl)cytosine
• CAS: 1454612-00-0
• 化学式: C₂₃H₃₅N₃O₁₀
• 分子量: 513.545
• InChiKey: YRDFWJHRZVKMHC-LMHBHQSJSA-N

物化性质

• 沸点：
  611.8±65.0 °C(predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  36.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  158.88
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N,N-4(ditert-butoxycarbonyl)-1-(2,3-O-isopropylidene-β-D-ribo-(5R)-hexofuranosyl)cytosine 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以74%的产率得到N,N-4(ditert-butoxycarbonyl)-1-(2,3-O-isopropylidene-5,6-oxiran-β-D-ribo-(5R)-hexofuranosyl)cytosine
  参考文献：
  名称：

  An Alternative Pathway to Ribonucleoside β-Hydroxyphosphonate Analogues and Related Prodrugs

  摘要：

  Nucleoside beta-(S)-hydroxyphosphonate analogues have recently proven to be interesting bioactive compounds as 5'-nucleotidase inhibitors. These derivatives were obtained in a pyrimidine series through an ex-chiral pool pathway or the stereoselective reduction of beta-ketophosphonate intermediate. Herein, an original synthesis of these compounds using nucleoside epoxide intermediates, containing either a pyrimidine or a purine as nucleobase, was explored and allowed the direct synthesis of the corresponding bis S-acyl-2-thioethyl (SATE) prodrugs.

  DOI：

  10.1021/ol402143y
• 作为产物：
  描述：

  N,N-4(ditert-butoxycarbonyl)-1-(2,3:5,6-di-O-isopropylidene-β-D-ribo-(5R)-hexofuranosyl)cytosine 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以38%的产率得到N,N-4(ditert-butoxycarbonyl)-1-(2,3-O-isopropylidene-β-D-ribo-(5R)-hexofuranosyl)cytosine
  参考文献：
  名称：

  An Alternative Pathway to Ribonucleoside β-Hydroxyphosphonate Analogues and Related Prodrugs

  摘要：

  Nucleoside beta-(S)-hydroxyphosphonate analogues have recently proven to be interesting bioactive compounds as 5'-nucleotidase inhibitors. These derivatives were obtained in a pyrimidine series through an ex-chiral pool pathway or the stereoselective reduction of beta-ketophosphonate intermediate. Herein, an original synthesis of these compounds using nucleoside epoxide intermediates, containing either a pyrimidine or a purine as nucleobase, was explored and allowed the direct synthesis of the corresponding bis S-acyl-2-thioethyl (SATE) prodrugs.

  DOI：

  10.1021/ol402143y