(6R)-6-C-[1,6-anhydro-2-O-benzyl-3-deoxy-β-D-xylo-hexopyrano-4-ulos-3-yl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pyranose | 201660-34-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: (6R)-6-C-[1,6-anhydro-2-O-benzyl-3-deoxy-β-D-xylo-hexopyrano-4-ulos-3-yl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pyranose
• 英文别名: (1R,3R,4R,5R)-3-[(R)-hydroxy-[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methyl]-4-phenylmethoxy-6,8-dioxabicyclo[3.2.1]octan-2-one
• CAS: 201660-34-6
• 化学式: C₂₅H₃₂O₁₀
• 分子量: 492.523
• InChiKey: DGOKBAFSQFHPCL-IBTGEWQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (6R)-6-C-[1,6-anhydro-2-O-benzyl-3-deoxy-β-D-xylo-hexopyrano-4-ulos-3-yl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-pyranose 在 calcium sulfate 、 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 4.5h， 生成
  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 三乙胺 作用下， 反应 15.0h， 生成 (6R)-6-C-[1,6-anhydro-2-O-benzyl-3-deoxy-β-D-xylo-hexopyrano-4-ulos-3-yl]-1,2:3,4-di-O-isopropylidene-α-D-galacto-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.