3-(2,4-dioxo-3,4-dihydro-pyrimidin-1-yl)-N-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1-yl)tetrahydrofuran-2-ylmethyl]propanamide | 1174386-74-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 2 '，5'-二脱氧核苷
• 英文名称: 3-(2,4-dioxo-3,4-dihydro-pyrimidin-1-yl)-N-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1-yl)tetrahydrofuran-2-ylmethyl]propanamide
• CAS: 1174386-74-3
• 化学式: C₁₇H₂₁N₅O₇
• 分子量: 407.383
• InChiKey: VYECYMIISAOYEZ-MISXGVKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.45
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  168.28
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  5-氨基-5-脱氧胸腺嘧啶脱氧核苷 、 3-(2,4-二氧代-3,4-二氢-1(2H)-嘧啶基)丙酸 在 N-甲基吗啉 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以64%的产率得到3-(2,4-dioxo-3,4-dihydro-pyrimidin-1-yl)-N-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1-yl)tetrahydrofuran-2-ylmethyl]propanamide
  参考文献：
  名称：

  Novel Acyclic Amide-Conjugated Nucleosides and Their Analogues

  摘要：

  An effective one-step synthesis of new amide-conjugated nucleosides and their analogues, in the presence of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as the condensing agent, is presented. Substrate subunits carrying carboxylic group were obtained by acidic hydrolysis of Michael-type adducts of various 5-substituted uracil derivatives to methyl acrylate. Amine substrate was synthesized by reduction of 1-(2'-cyanoethyl)thymine with sodium borohydride in the presence of nickel (II) chloride as catalyst. Other applied amine substrates were 5'-amino-5'-deoxythymidine and 5-aminouracil.

  DOI：

  10.1080/15257770902736467