1,6:2,3-dianhydro-3-C-[(1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose-1',4-acetonide | 270923-11-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,6:2,3-dianhydro-3-C-[(1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose-1',4-acetonide
• CAS: 270923-11-0
• 化学式: C₄₄H₄₈O₁₀
• 分子量: 736.859
• InChiKey: XPCHDSCMOMYJJF-MCVGVUQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.14
• 重原子数：
  54.0
• 可旋转键数：
  14.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  95.6
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1,6:2,3-dianhydro-3-C-[(1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose-1',4-acetonide 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以75%的产率得到1,6:2,3-dianhydro-3-C-[(1S)-2,6-anhydro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose-1',4-acetonide
  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：

  1,6-anhydro-3-C-[(1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-D-gulo-heptitol-1-C-yl]-2,3-dideoxy-β-D-glycero-hex-2-en-4-ulopyranose 在 叔丁基过氧化氢 、 sodium tetrahydroborate 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 21.0h， 生成 1,6:2,3-dianhydro-3-C-[(1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose-1',4-acetonide
  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