4-O-acetyl-1,6:2,3-dianhydro-3-C-[(1S)-1,3,4,5,7-penta-O-acetyl-2,6-anhydro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose | 270923-08-5

• 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: 4-O-acetyl-1,6:2,3-dianhydro-3-C-[(1S)-1,3,4,5,7-penta-O-acetyl-2,6-anhydro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose
• 英文别名: [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-[(S)-acetyloxy-[(1R,2R,4S,5S,6R)-5-acetyloxy-3,8,9-trioxatricyclo[4.2.1.02,4]nonan-4-yl]methyl]oxan-2-yl]methyl acetate
• CAS: 270923-08-5
• 化学式: C₂₅H₃₂O₁₆
• 分子量: 588.519
• InChiKey: XRIBCGHQHWJODA-GOLJSDFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  41
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  198
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  4-O-acetyl-1,6:2,3-dianhydro-3-C-[(1S)-1,3,4,5,7-penta-O-acetyl-2,6-anhydro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose 在 氨 、 三氟乙酸 作用下， 反应 31.0h， 生成 2,3-anhydro-3-C-[(1S)-2,6-anhydro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose
  参考文献：
  名称：

  Convergent syntheses of C(1→3)-linked disaccharides starting from isolevoglucosenone

  摘要：

  Nucleophilic addition (Nu-Mf) to isolevoglucosenone 1 generates enolates stereospecifically (exo face addition) that can be reacted with sugar-derived aldehydes to give C(1-->3)-linked disaccharide precursors with high diastereoselectivity. Limitations of the method arising from unfavorable aldolate stability can be overcome by using Et2AlI as the nucleophile. This leads to products of Baylis-Hillmann condensations. One example is presented and has led to the preparation of 2,3-anhydro-3-C-[(1S)-2,6-anhydro-D-glycero-D-gulo-heptitol-1-C-yl]-beta-D-gulo-pyranose 5. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00492-9
• 作为产物：
  描述：

  乙酸酐 、 1,6:2,3-dianhydro-3-C-[(1S)-2,6-anhydro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 15.0h， 以95%的产率得到4-O-acetyl-1,6:2,3-dianhydro-3-C-[(1S)-1,3,4,5,7-penta-O-acetyl-2,6-anhydro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose
  参考文献：
  名称：

  Convergent syntheses of C(1→3)-linked disaccharides starting from isolevoglucosenone

  摘要：

  Nucleophilic addition (Nu-Mf) to isolevoglucosenone 1 generates enolates stereospecifically (exo face addition) that can be reacted with sugar-derived aldehydes to give C(1-->3)-linked disaccharide precursors with high diastereoselectivity. Limitations of the method arising from unfavorable aldolate stability can be overcome by using Et2AlI as the nucleophile. This leads to products of Baylis-Hillmann condensations. One example is presented and has led to the preparation of 2,3-anhydro-3-C-[(1S)-2,6-anhydro-D-glycero-D-gulo-heptitol-1-C-yl]-beta-D-gulo-pyranose 5. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00492-9