2,3,4-tri-O-acetyl-1-chloro-1-deoxy-α-D-glucopyranuron-N-phenylamide | 474426-99-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4-tri-O-acetyl-1-chloro-1-deoxy-α-D-glucopyranuron-N-phenylamide
• 英文别名: [(2R,3R,4S,5S,6S)-3,5-diacetyloxy-2-chloro-6-(phenylcarbamoyl)oxan-4-yl] acetate
• CAS: 474426-99-8
• 化学式: C₁₈H₂₀ClNO₈
• 分子量: 413.812
• InChiKey: ZCJXWFJQCTVBIN-KSWRQPAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-1-chloro-1-deoxy-α-D-glucopyranuron-N-phenylamide 在 叠氮基三甲基硅烷 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 生成 2,3,4-tri-O-acetyl-1-azido-1-deoxy-α-D-glucopyranuric acid N-phenylamide
  参考文献：
  名称：

  Synthesis of α-Glucuronic Acid and Amide Derivatives in the Presence of a Participating 2-Acyl Protecting Group

  摘要：

  [GRAPHICS]Participating acyl groups located at C-2 in glucosyl and related donors generally promote formation of 1,2-trans-glycosides. Reactions of some glucuronic acid donors with TMSN3/SnCl4 or ROH/SnCl4 gave only the 1,2-cis-glycoside. The stereoselectivity is consistent with participation of the C-6 group. The methodology was used for the synthesis of a Kdn2en mimetic with the alpha-configuration.

  DOI：

  10.1021/ol026629j
• 作为产物：
  描述：

  [(2S,3R,4S,5S,6S)-2,3,5-triacetyloxy-6-(phenylcarbamoyl)oxan-4-yl] acetate 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 生成 2,3,4-tri-O-acetyl-1-chloro-1-deoxy-α-D-glucopyranuron-N-phenylamide
  参考文献：
  名称：

  Synthesis of α-Glucuronic Acid and Amide Derivatives in the Presence of a Participating 2-Acyl Protecting Group

  摘要：

  [GRAPHICS]Participating acyl groups located at C-2 in glucosyl and related donors generally promote formation of 1,2-trans-glycosides. Reactions of some glucuronic acid donors with TMSN3/SnCl4 or ROH/SnCl4 gave only the 1,2-cis-glycoside. The stereoselectivity is consistent with participation of the C-6 group. The methodology was used for the synthesis of a Kdn2en mimetic with the alpha-configuration.

  DOI：

  10.1021/ol026629j

文献信息

• The synthesis of cyclic imidates from amides of glucuronic acid and investigation of glycosidation reactions
  作者：Linda Cronin、Manuela Tosin、Helge Müller-Bunz、Paul V. Murphy

  DOI：10.1016/j.carres.2006.10.023

  日期：2007.1

  The synthesis of novel cyclic glycosyl imidates and an investigation of their potential as donors in glycosidation reactions is described. The results show that 1,2-cis glycosides obtained from the reactions of glycosyl acetates or cyclic imidates, each derived from amides of glucuronic acid, result from the anomerisation of initially formed 1,2-trans glycosides.

  描述了新型环状糖基酰亚胺的合成及其在糖基化反应中作为供体的潜力的研究。结果表明，从乙酸糖基酯或环状酰亚胺化物的反应获得的1，2-顺式糖苷均衍生自最初形成的1，2-反式糖苷，它们各自衍生自葡糖醛酸的酰胺。