phenyl 5-O-benzyl-3-C-[(benzyloxy)methyl]-2,3-dideoxy-1-seleno-β-D-threo-pentofuranoside

• 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: phenyl 5-O-benzyl-3-C-[(benzyloxy)methyl]-2,3-dideoxy-1-seleno-β-D-threo-pentofuranoside
• 英文别名: (2S,3S,5S)-2,3-bis(phenylmethoxymethyl)-5-phenylselanyloxolane
• 化学式: C₂₆H₂₈O₃Se
• 分子量: 467.467
• InChiKey: CRMXIBURTZBCOW-DMDYGQEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ((2S,3S,5S)-3-Hydroxymethyl-5-methoxy-tetrahydro-furan-2-yl)-methanol 在 三氟化硼乙醚 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 phenyl 5-O-benzyl-3-C-[(benzyloxy)methyl]-2,3-dideoxy-1-seleno-β-D-threo-pentofuranoside
  参考文献：
  名称：

  Stereoselective Synthesis of Branched and Bicyclo 2‘,3‘-Dideoxy-threo-furanosyl Nucleosides from Pyranoses Using a Ring Contraction Reaction as the Key Step

  摘要：

  Bicycle nucleoside 21 and the branched-chain nucleoside 26 have been stereoselectively synthesized (alpha:beta = 1:4) from a common intermediate 14, which was obtained from methyl 4,6-O-benzylidene-2-deoxy-3-O-triflyl-alpha-D-arabino-pyranoside (13) through a ring contraction reaction. The branched nucleoside 26 was obtained with an alpha:beta selectivity of 1:4 using either electrophilic selenium or sulfur reagents. In contrast the bicycle nucleoside 21 was only obtained using the phenylthio derivative 20. The selenium reagents resulted in predominant formation of the alpha isomer.

  DOI：

  10.1021/jo961806d

文献信息

• Stereoselective Synthesis of Branched and Bicyclo 2‘,3‘-Dideoxy-<i>threo</i>-furanosyl Nucleosides from Pyranoses Using a Ring Contraction Reaction as the Key Step
  作者：Mohamed Kassou、Sergio Castillón

  DOI：10.1021/jo961806d

  日期：1997.5.1

  Bicycle nucleoside 21 and the branched-chain nucleoside 26 have been stereoselectively synthesized (alpha:beta = 1:4) from a common intermediate 14, which was obtained from methyl 4,6-O-benzylidene-2-deoxy-3-O-triflyl-alpha-D-arabino-pyranoside (13) through a ring contraction reaction. The branched nucleoside 26 was obtained with an alpha:beta selectivity of 1:4 using either electrophilic selenium or sulfur reagents. In contrast the bicycle nucleoside 21 was only obtained using the phenylthio derivative 20. The selenium reagents resulted in predominant formation of the alpha isomer.