1-2',3',5'-tri-O-benzoyl-β-D-ribopentofuranosyl-5-(ethoxycarbonyl)-4,6-diphenylpyrimidin-2-thione | 1417444-57-5

• 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: 1-2',3',5'-tri-O-benzoyl-β-D-ribopentofuranosyl-5-(ethoxycarbonyl)-4,6-diphenylpyrimidin-2-thione
• 英文别名: ethyl 1-[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)oxolan-2-yl]-4,6-diphenyl-2-sulfanylidenepyrimidine-5-carboxylate
• CAS: 1417444-57-5
• 化学式: C₄₅H₃₆N₂O₉S
• 分子量: 780.855
• InChiKey: MEVVCEILQQCMPN-ZTWIBWFSSA-N

物化性质

• 沸点：
  860.9±75.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  162
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-oxo-4,6-diphenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester 在 劳森试剂 、 三氟化硼乙醚 、 甲烷 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙腈 、 苯 为溶剂， 反应 4.0h， 生成 1-2',3',5'-tri-O-benzoyl-β-D-ribopentofuranosyl-5-(ethoxycarbonyl)-4,6-diphenylpyrimidin-2-thione
  参考文献：
  名称：

  Synthesis of novel nucleosides and stereoselectivity of N-glycosidation

  摘要：

  An efficient synthetic route for novel nucleosides has been realized. We report the formation of alpha-isomers in spite of neighboring group participation by the benzoyl group at the 2-position in N-glycosidation as well as discuss the stereoselectivity observed. We also found that non-silylated pyrimidin-2(1H)-ones and pyrimidin-2(1H)-thiones having aromatic structures reacted with 1-fluororibose in the presence of a Lewis acid to give the corresponding nucleosides in good to high yield. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.017

文献信息

• Synthesis of novel nucleosides and stereoselectivity of N-glycosidation
  作者：Kyosuke Michigami、Satoshi Uchida、Miho Adachi、Masahiko Hayashi

  DOI：10.1016/j.tet.2012.11.017

  日期：2013.1

  An efficient synthetic route for novel nucleosides has been realized. We report the formation of alpha-isomers in spite of neighboring group participation by the benzoyl group at the 2-position in N-glycosidation as well as discuss the stereoselectivity observed. We also found that non-silylated pyrimidin-2(1H)-ones and pyrimidin-2(1H)-thiones having aromatic structures reacted with 1-fluororibose in the presence of a Lewis acid to give the corresponding nucleosides in good to high yield. (c) 2012 Elsevier Ltd. All rights reserved.