2,3,5-tri-O-benzoyl-1-bromo-1-cyano-1-dehydro-1-deoxy-D-ribofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5-tri-O-benzoyl-1-bromo-1-cyano-1-dehydro-1-deoxy-D-ribofuranose
• 英文别名: 2,3,5-tri-O-benzoyl-1-α-bromo-D-ribofuranosyl cyanide；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-bromo-5-cyanooxolan-2-yl]methyl benzoate
• 化学式: C₂₇H₂₀BrNO₇
• 分子量: 550.362
• InChiKey: XCVJLNUSYSJOGE-ANAFOTAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  硫脲 、 2,3,5-tri-O-benzoyl-1-bromo-1-cyano-1-dehydro-1-deoxy-D-ribofuranose 在 盐酸 作用下， 生成 1-thiahydantocidin
  参考文献：
  名称：

  Concise Approach to 1-thiaHydantocidin

  摘要：

  The synthesis of 1-thiaHydantocidin, a close analog of the total herbicide Hydantocidin, is described starting from 2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl cyanide.

  DOI：

  10.1080/00397919608003864
• 作为产物：
  描述：

  2,3,5-tri-O-benzoyl-β-D-ribofuranosyl-1-carbonitrile 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 0.58h， 以62%的产率得到2,3,5-tri-O-benzoyl-1-bromo-1-cyano-1-dehydro-1-deoxy-D-ribofuranose
  参考文献：
  名称：

  Synthesis and structure determination of the first 1′-C-cyano-β-D-nucleosides

  摘要：

  The 1'-cyano -2',3'-D-unsaturated nucleoside 8 was synthesised according to the following steps. Photobromination of the ribofuranosyl cyanide 1 using N-bromosuccinimide (NBS) as a radical source gave the two isomers of the new C-1 gem disubstituted sugar 2. Its condensation with silylated thymine afforded the blocked nucleoside 3, the stereochemistry and molecular shape of which were deduced from NMR studies and molecular simulation. After deprotection of 3 into 4, thiocarbonylation of the silylated derivative 5, followed by olefination of 6, led to 7 which was deblocked to the 1'-cyano substituted d4T 8.

  DOI：

  10.1016/s0040-4020(01)96264-7