2,6-anhydro-1,4,5-tri-O-benzyl-3-deoxy-3-C-formyl-D-erythro-hex-2-enitol | 374688-17-2

• 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: 2,6-anhydro-1,4,5-tri-O-benzyl-3-deoxy-3-C-formyl-D-erythro-hex-2-enitol
• 英文别名: (3R,4S)-3,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-5-carbaldehyde
• CAS: 374688-17-2
• 化学式: C₂₈H₂₈O₅
• 分子量: 444.527
• InChiKey: FJJZEHGKYSPWSW-IZLXSDGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-anhydro-1,4,5-tri-O-benzyl-3-deoxy-3-C-formyl-D-erythro-hex-2-enitol 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以88%的产率得到
  参考文献：
  名称：

  Syntheses of Acyclo-C-nucleosides by Ring Transformation of 2(3)-Formyl-glycals

  摘要：

  The 2(3)-formyl-glycals 2, 4, 6 react with hydrazine hydrate to furnish the C-(1H-pyrazol-3-yl)alditoles 7, 8, 9. Treatment of 2, 4, 6 with cyanoacetamide provides the 2(3)(2-aminocarbonyl-2-cyano-vinyl)-1,5(2,6)-anhydro-2(3)-deoxy-hex-1-enitols 10, 13, 15, which are converted into the polyhydroxyalkyl 2-amino-nicotinamides 11, 14, 16 and pyridinecarbonitriles 12, respectively.

  DOI：

  10.1002/prac.19983400407
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 在 三氯氧磷 作用下， 以47%的产率得到2,6-anhydro-1,4,5-tri-O-benzyl-3-deoxy-3-C-formyl-D-erythro-hex-2-enitol
  参考文献：
  名称：

  Syntheses of Acyclo-C-nucleosides by Ring Transformation of 2(3)-Formyl-glycals

  摘要：

  The 2(3)-formyl-glycals 2, 4, 6 react with hydrazine hydrate to furnish the C-(1H-pyrazol-3-yl)alditoles 7, 8, 9. Treatment of 2, 4, 6 with cyanoacetamide provides the 2(3)(2-aminocarbonyl-2-cyano-vinyl)-1,5(2,6)-anhydro-2(3)-deoxy-hex-1-enitols 10, 13, 15, which are converted into the polyhydroxyalkyl 2-amino-nicotinamides 11, 14, 16 and pyridinecarbonitriles 12, respectively.

  DOI：

  10.1002/prac.19983400407

文献信息

• A Facile Synthesis of Acyclo-C-nucleoside Analogues from 2(3)-Formylglycals
  作者：Ivo Rudloff、Manfred Michalik、Alina Montero、Klaus Peseke

  DOI：10.1055/s-2001-16761

  日期：——

  The reaction of 2(3)-formylglycals with malononitrile afforded push-pull butadienes with a sugar moiety. The treatment of these branched-chain sugars with ammonia yielded nicotinonitrile acyclo-C-nucleosides. Furthermore, a one step ring transformation of 2(3)-formylglycals with N-aryl-acetoacetanilides to give pyridone acyclo-C-nucleosides is described.

  2(3)-甲醛糖醛与马隆腈的反应生成了带有糖基的推拉型丁二烯。将这些支链糖与氨反应得到尼古丁腈非环C-核苷。此外，还描述了一步法将2(3)-甲醛糖醛与N-芳基-乙酰乙酸苯胺进行环转换，得到吡啶酮非环C-核苷。
• Rudloff, Ivo; Bari, Ahmed; Feist, Holger, Zeitschrift fur Naturforschung, B: Chemical Sciences, 2004, vol. 59, # 4, p. 398 - 405
  作者：Rudloff, Ivo、Bari, Ahmed、Feist, Holger、Michalik, Manfred、Reinke, Helmut、Peseke, Klaus

  DOI：——

  日期：——
• Syntheses of Acyclo-C-nucleosides by Ring Transformation of 2(3)-Formyl-glycals
  作者：Ivo Rudloff、Klaus Peseke、Helmut Reinke

  DOI：10.1002/prac.19983400407

  日期：——

  The 2(3)-formyl-glycals 2, 4, 6 react with hydrazine hydrate to furnish the C-(1H-pyrazol-3-yl)alditoles 7, 8, 9. Treatment of 2, 4, 6 with cyanoacetamide provides the 2(3)(2-aminocarbonyl-2-cyano-vinyl)-1,5(2,6)-anhydro-2(3)-deoxy-hex-1-enitols 10, 13, 15, which are converted into the polyhydroxyalkyl 2-amino-nicotinamides 11, 14, 16 and pyridinecarbonitriles 12, respectively.