2-amino-5-(1,2,4-tri-O-benzyl-D-lyxo-1,2,3,4-tetrahydroxybutyl)pyrimidine

• 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: 2-amino-5-(1,2,4-tri-O-benzyl-D-lyxo-1,2,3,4-tetrahydroxybutyl)pyrimidine
• 英文别名: (2R,3S,4R)-4-(2-aminopyrimidin-5-yl)-1,3,4-tris(phenylmethoxy)butan-2-ol
• 化学式: C₂₉H₃₁N₃O₄
• 分子量: 485.583
• InChiKey: KHYLXQCYOSUPGX-FCEKVYKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  99.7
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran-5-carbaldehyde 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 12.0h， 以86%的产率得到2-amino-5-(1,2,4-tri-O-benzyl-D-lyxo-1,2,3,4-tetrahydroxybutyl)pyrimidine
  参考文献：
  名称：

  An improved synthesis of pyrimidine- and pyrazole-based acyclo-C-nucleosides as carbohybrids

  摘要：

  The synthesis of pyrimidine- and pyrazole-based acyclo-C-nucleosides as carbohybrids was optimized and developed. The synthesis of acyclic polyol-fused pyrimidines was achieved in good to excellent yield with high purity by the cyclocondensation of 2-C-formyl glycals and various amidines using K2CO3 as inorganic base in co-solvent system. In comparison, the syntheses of pyrazole-based acyclo-C-nucleosides were accomplished simply by the cyclocondensation of 2-C-formyl glycals with hydrazine hydrate at room temperature and with phenyl hydrazine at refluxing temperature in ethanol. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.032

文献信息

• SYNTHESIS OF PRECURSORS FOR NEW PYRIMIDINE ACYCLO-<i>C</i>-NUCLEOSIDE ANALOGUES BY RING TRANSFORMATION OF 2-FORMYLGALACTAL ^*,†
  作者：Alina Montero、Holger Feist、Manfred Michalik、José Quincoces、Klaus Peseke

  DOI：10.1081/car-120013499

  日期：2002.9.23

  5-(1,2,4-tri-O-benzyl-d-lyxo-1,2,3,4-tetrahydroxybutyl)pyrimidines 2–4. Treatment of 1 with 2-aminobenzimidazole and 3-amino-1,2,4-triazole, respectively, afforded 3-(1,2,4-tri-O-benzyl-d-lyxo-1,2,3,4-tetrahydroxybutyl)benzo[4,5]imidazo[1,2-a]pyrimidine (5) and 6-(1,2,4-tri-O-benzyl-d-lyxo-1,2,3,4-tetrahydroxybutyl)-[1,2,4]triazolo[1,5-a]pyrimidine (6).

  2- formylgalactal反应1，呈现为与推挽官能的不饱和糖衍生物与胍和脒鎓盐，分别在碱性条件下进行，得到的取代的5-（1,2,4-三- ø -苄基d - L-来苏-1,2,3,4-四羟基丁基）嘧啶2 - 4。分别用2-氨基苯并咪唑和3-氨基-1,2,4-三唑处理1，得到3-（1,2,4-三-O-苄基-d - lyxo -1,2,3,4-四羟基丁基）苯并[4,5]咪唑并[1,2- a ]嘧啶（5）和6-（1,2,4-tri- O-苄基-d - lyxo -1,2,3,4-四羟基丁基）-[1,2,4]三唑并[1,5- a ]嘧啶（6）。