1,4-anhydro-3-O-benzyl-α-D-xylopyranose | 213963-76-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,4-anhydro-3-O-benzyl-α-D-xylopyranose
• CAS: 213963-76-9
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: JXIZZJXSIZJEFW-WISYIIOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.69
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,4-anhydro-3-O-benzyl-α-D-xylopyranose 在 吡啶 作用下， 生成 2-O-acetyl-1,4-anhydro-3-O-benzyl-α-D-xylopyranose
  参考文献：
  名称：

  Two novel synthetic methods for 1,4-anhydro-α-d-xylopyranose derivatives

  摘要：

  Two novel methods for the syntheses of 1,4-anhydro-3-O-benzyl-2-O-pivaloyl- (1) and 2-O-acetyl-1,4-anhydro-3-O-benzyl-alpha-D-xylopyranose (2), starting materials for synthesizing stereoregular beta-(1-->5)-xylofuranan by ring-opening polymerization are reported. Both synthetic routes start from D-xylopyranose, involve nine reaction steps, and give approximately 30-35% overall yields. The key reaction in the novel synthetic routes is the intramolecular nucleophilic attack of C-1 oxyanion on the C-5 position of 3-O-benzyl-5-O-(p-toluenesulfonyl)-alpha-D-xylofuranose (10), resulting in 1,5-acetal bond formation in high yield. The present synthetic routes enable us to prepare 1,4-anhydro-alpha-D-xylopyranose derivatives having different substituents at the 2-O- and the 3-O-positions. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00135-9
• 作为产物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 在 吡啶 、 四甲基氢氧化铵 、 水 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 1,4-anhydro-3-O-benzyl-α-D-xylopyranose
  参考文献：
  名称：

  Two novel synthetic methods for 1,4-anhydro-α-d-xylopyranose derivatives

  摘要：

  Two novel methods for the syntheses of 1,4-anhydro-3-O-benzyl-2-O-pivaloyl- (1) and 2-O-acetyl-1,4-anhydro-3-O-benzyl-alpha-D-xylopyranose (2), starting materials for synthesizing stereoregular beta-(1-->5)-xylofuranan by ring-opening polymerization are reported. Both synthetic routes start from D-xylopyranose, involve nine reaction steps, and give approximately 30-35% overall yields. The key reaction in the novel synthetic routes is the intramolecular nucleophilic attack of C-1 oxyanion on the C-5 position of 3-O-benzyl-5-O-(p-toluenesulfonyl)-alpha-D-xylofuranose (10), resulting in 1,5-acetal bond formation in high yield. The present synthetic routes enable us to prepare 1,4-anhydro-alpha-D-xylopyranose derivatives having different substituents at the 2-O- and the 3-O-positions. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00135-9