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 | 270923-06-3

• 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
• 英文别名: (1R,2R,4S,5S,6R)-4-[(S)-hydroxy-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]-3,8,9-trioxatricyclo[4.2.1.02,4]nonan-5-ol
• CAS: 270923-06-3
• 化学式: C₄₁H₄₄O₁₀
• 分子量: 696.794
• InChiKey: OJBXKHCSLDTRMY-LVUGXWFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  51
• 可旋转键数：
  15
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  10

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 在 氨 、 sodium 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 15.33h， 生成 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：

  isolevoglucosenone 在 叔丁基过氧化氢 、 sodium tetrahydroborate 、 二乙基碘化铝 、 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 、 甲苯 为溶剂， 反应 10.0h， 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
  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

文献信息

• Convergent syntheses of C(1→3)-linked disaccharides starting from isolevoglucosenone
  作者：Yao-Hua Zhu、Raynald Demange、Pierre Vogel

  DOI：10.1016/s0957-4166(99)00492-9

  日期：2000.1

  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.