[[(E)-4-(2-oxo-6-pentylfuro[2,3-d]pyrimidin-3-yl)but-2-enyl]-(propan-2-yloxycarbonyloxymethoxy)phosphoryl]oxymethyl propan-2-yl carbonate | 1314531-99-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃[2,3-d]嘧啶
• 英文名称: [[(E)-4-(2-oxo-6-pentylfuro[2,3-d]pyrimidin-3-yl)but-2-enyl]-(propan-2-yloxycarbonyloxymethoxy)phosphoryl]oxymethyl propan-2-yl carbonate
• CAS: 1314531-99-1
• 化学式: C₂₅H₃₇N₂O₁₁P
• 分子量: 572.549
• InChiKey: SEHYGVMCSYDKRR-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  39
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  149
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  3-crotyl-6-n-pentyl-2,3-dihydrofuro[2,3-d]pyrimidin-2(3H)-one 、 bis-POC-allylphosphonate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以49%的产率得到[[(E)-4-(2-oxo-6-pentylfuro[2,3-d]pyrimidin-3-yl)but-2-enyl]-(propan-2-yloxycarbonyloxymethoxy)phosphoryl]oxymethyl propan-2-yl carbonate
  参考文献：
  名称：

  Expeditious convergent procedure for the preparation of bis(POC) prodrugs of new (E)-4-phosphono-but-2-en-1-yl nucleosides

  摘要：

  A series of unsaturated acyclonucleoside bis(POC) prodrugs of E configuration were synthesized through an expeditious, highly efficient and stereoselective one-step procedure from corresponding bis(POC)allylphosphonate through Ru catalyzed cross-coupling metathesis reaction. The [RuCl(2)(PCy(3))(SIPr)(Inde-nylidene)] and [RuCl(2)(PCy(3))(IMes)(benzylidene)] catalysts were employed; the unsaturated ANP were used bore C5-halovinyl uracil, C5-dihalovinyluracil or furanopyrimidine motifs. The chemical cleavage of biolabile (POC) group is a useful pathway to acid phosphonate derivatives. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.017