1-(α-D-2',3',5'-tri-O-benzyl-lyxofuranosyl)thymine | 1198760-98-3

• 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-lyxofuranosyl)thymine
• 英文别名: 1-(β-D-2',3',5'-tri-O-benzyl-lyxosyl)thymine；Bn(-2)[Bn(-3)][Bn(-5)]Lyxf(b)-thymin-1-yl；1-[(2R,3S,4S,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1198760-98-3
• 化学式: C₃₁H₃₂N₂O₆
• 分子量: 528.605
• InChiKey: YAPVFZFSDDFVSE-GPRIDDLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  86.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-methyl-1-[(1S,2S,3S,4R)-2,3,5-tris-benzyloxy-1-ethylsulfanyl-4-hydroxy-pentyl]-1H-pyrimidine-2,4-dione 在 dimethyl(methylthio)sulfonium tetrafluoroborate 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到1-(α-D-2',3',5'-tri-O-benzyl-lyxofuranosyl)thymine
  参考文献：
  名称：

  A Stereoselective Approach to Nucleosides and 4′-Thioanalogues from Acyclic Precursors

  摘要：

  D- and L-nucleosides and analogues thereof, including the 4'-thionucleoside series, are one of the most important biological and pharmaceutically active classes of compounds. A novel approach to their synthesis from chiral acyclic thioaminal, bearing the nucleobase, is described.

  DOI：

  10.1021/ja905452f

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.
• A Stereoselective Approach to Nucleosides and 4′-Thioanalogues from Acyclic Precursors
  作者：Daniel Chapdelaine、Benoit Cardinal-David、Michel Prévost、Marc Gagnon、Isabelle Thumin、Yvan Guindon

  DOI：10.1021/ja905452f

  日期：2009.12.2

  D- and L-nucleosides and analogues thereof, including the 4'-thionucleoside series, are one of the most important biological and pharmaceutically active classes of compounds. A novel approach to their synthesis from chiral acyclic thioaminal, bearing the nucleobase, is described.