1-(β-D-2',3',5'-tri-O-benzyl-ribosyl)thymine | 147103-50-2

• 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-(β-D-2',3',5'-tri-O-benzyl-ribosyl)thymine
• 英文别名: Bn(-2)[Bn(-3)][Bn(-5)]Ribf(b)-thymin-1-yl；1-[(2R,3R,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 147103-50-2
• 化学式: C₃₁H₃₂N₂O₆
• 分子量: 528.605
• InChiKey: YAPVFZFSDDFVSE-NODMTMHWSA-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,2R,3R,4R)-2,3,5-tris-benzyloxy-1-benzylsulfanyl-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99%的产率得到1-(β-D-2',3',5'-tri-O-benzyl-ribosyl)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

• Stereoselective Synthesis of 1,2-<i>cis</i>-<i>N</i>-Glycosides by the<i>N</i>-Bromosuccinimide Promoted Reaction of Thioglycosides with Silylated Pyrimidme Bases
  作者：Hideyuki Sugimura、Ikuyo Muramoto、Tadashi Nakamura、Kenji Osumi

  DOI：10.1246/cl.1993.169

  日期：1993.1

  The coupling of O-benzylated 1-thioglycosides, derived from d-glucose, d-mannose, d-ribose, d-xylose, and d-arabinose, with silylated pyrimidme bases by activation with N-bromosuccinimide uniformly afforded the corresponding 1,2-cis-N-glycosides with good selectivity.

  通过N-溴代琥珀酰亚胺活化，将源自d-葡萄糖、d-甘露糖、d-核糖、d-木糖和d-阿拉伯糖的O-苄基1-硫代糖苷与硅烷化的嘧啶碱结合，可以均匀地得到具有良好选择性的相应1,2-顺式-N-糖苷。
• The stereocontrolled synthesis of 1,2-cis furanosyl nucleosides via a novel anomeric activation
  作者：S Hanessian

  DOI：10.1016/00404-0399(50)1179l-

  日期：1995.8.14

  The coupling of 2-(2',3',5'-tri-O-benzyl-D-ribofuranosyloxy)-3-methoxypyridine as well as 2-(2',3',5'-tri-O-benzyl-D-ribofuranosyl with silylated pyrimidine bases by activation with trimethylsilyl trifluoromethanesulfonate and silver triflate respectively affords the corresponding 1,2-cis nucleosides with high selectivity.