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-ribo-hex-4-ulopyranose | 270923-05-2

• 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-ribo-hex-4-ulopyranose
• CAS: 270923-05-2
• 化学式: C₄₁H₄₂O₁₀
• 分子量: 694.778
• InChiKey: MGPYXQJWGPTLGF-PTTIQEOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  51.0
• 可旋转键数：
  15.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  114.44
• 氢给体数：
  1.0
• 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-ribo-hex-4-ulopyranose 在 sodium tetrahydroborate 、 二乙胺基三氟化硫 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1,6:2,3-dianhydro-3-C-[(1R)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-fluoro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose
  参考文献：
  名称：

  Synthesis and Solution Conformational Analysis of 2,3-Anhydro-3-C-[(1R)-2,6-anhydro-1-deoxy-1-fluoro-d-glycero-d-gulo- heptitol-1-C-yl]-β-d-gulo-furanose:  First Example of a Monofluoromethylene-Linked C-Disaccharide

  摘要：

  Condensation of 2,3,4,6-tetra-O-benzyl-beta -D-glueopyranosylcarbaldehyde with isolevoglucosenone induced by Et2AlI, followed by epoxidation, gave an aldol that was fluorinated into a monofluoro-methylene C-glucopyranoside that was converted into the title C-disaccharide 1. Its conformational behavior in water has been studied by using a combination of NMR spectroscopy (J and NOE data) and molecular mechanics calculations.

  DOI：

  10.1021/jo0102462
• 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 作用下， 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-ribo-hex-4-ulopyranose
  参考文献：
  名称：

  Synthesis and Solution Conformational Analysis of 2,3-Anhydro-3-C-[(1R)-2,6-anhydro-1-deoxy-1-fluoro-d-glycero-d-gulo- heptitol-1-C-yl]-β-d-gulo-furanose:  First Example of a Monofluoromethylene-Linked C-Disaccharide

  摘要：

  Condensation of 2,3,4,6-tetra-O-benzyl-beta -D-glueopyranosylcarbaldehyde with isolevoglucosenone induced by Et2AlI, followed by epoxidation, gave an aldol that was fluorinated into a monofluoro-methylene C-glucopyranoside that was converted into the title C-disaccharide 1. Its conformational behavior in water has been studied by using a combination of NMR spectroscopy (J and NOE data) and molecular mechanics calculations.

  DOI：

  10.1021/jo0102462

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.