1-(α-D-2',3',5'-tri-O-benzyl-ribofuranosyl)cytosine | 3574-09-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(α-D-2',3',5'-tri-O-benzyl-ribofuranosyl)cytosine
• 英文别名: 4-amino-1-(O²,O³,O⁵-tribenzyl-α-D-ribofuranosyl)-1H-pyrimidin-2-one；4-amino-1-[(2S,3R,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]pyrimidin-2-one
• CAS: 3574-09-2
• 化学式: C₃₀H₃₁N₃O₅
• 分子量: 513.593
• InChiKey: LGQHGCYXYLWDQU-PXTYPYQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  95.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3,5-三-O-(苯基甲基)-D-呋喃核糖 、 4-(1,1,1,3,3,3-Hexamethyl-disilazan-2-yl)-2-trimethylsilanyloxy-pyrimidine 在 二甲基溴化硼 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以93%的产率得到1-(α-D-2',3',5'-tri-O-benzyl-ribofuranosyl)cytosine
  参考文献：
  名称：

  Synthesis of 1′,2′-cis-Nucleoside Analogues: Evidence of Stereoelectronic Control for S_N2 Reactions at the Anomeric Center of Furanosides

  摘要：

  We are reporting a highly diastereoselective route to 1 ',2 '-cis-nucleoside analogues in the D-ribo, D-lyxo, D-xylo, and D-arabinoside series. Five-membered ring lactols undergo highly selective N-glycosidation reactions in the presence of dimethylboron bromide with different silylated nucleobases. Stereoelectronic control plays a crucial role for the observed induction, and the products are proposed to be formed through S(N)2 "exploded" transition states. This approach shows great potential considering its simplicity and selectivity for the synthesis of nucleoside analogues, an important class of molecules in medicinal chemistry.

  DOI：

  10.1021/ja104429y

文献信息

• Synthesis of 1′,2′-<i>cis</i>-Nucleoside Analogues: Evidence of Stereoelectronic Control for S_N2 Reactions at the Anomeric Center of Furanosides
  作者：Michel Prévost、Olivier St-Jean、Yvan Guindon

  DOI：10.1021/ja104429y

  日期：2010.9.8

  We are reporting a highly diastereoselective route to 1 ',2 '-cis-nucleoside analogues in the D-ribo, D-lyxo, D-xylo, and D-arabinoside series. Five-membered ring lactols undergo highly selective N-glycosidation reactions in the presence of dimethylboron bromide with different silylated nucleobases. Stereoelectronic control plays a crucial role for the observed induction, and the products are proposed to be formed through S(N)2 "exploded" transition states. This approach shows great potential considering its simplicity and selectivity for the synthesis of nucleoside analogues, an important class of molecules in medicinal chemistry.