4-O-benzoyl-3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranose | 121330-36-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-benzoyl-3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranose
• 英文别名: 4-O-Benzoyl-3-O-benzyl-2,6-dideoxy-D-arabino-hexopyranose；[(2R,3R,4R,6S)-6-hydroxy-2-methyl-4-phenylmethoxyoxan-3-yl] benzoate
• CAS: 121330-36-7
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: NWVACPXWPIEZTK-DQEVTTJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氘代甲醇-d 、 4-O-benzoyl-3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranose 在 diclazuril 、 sodium 作用下， 生成 Methyl 3-O-benzyl-2,6-dideoxy-2,2'-dideuterio-β-D-arabino-hexopyranoside
  参考文献：
  名称：

  Negative-Ion Mass Spectrometry of Carbohydrates. A Mechanistic Study of the Fragmentation Reactions of Dideoxy Sugars

  摘要：

  Hydroxyl group deprotonation of the alpha and beta anomers of methyl 3-O-benzyl-2,6-dideoxy-D-arabino-hexopyranoside (1 and 2) occurs readily in the gas phase to produce the corresponding anions 3 and 4, respectively. Collisionally activated dissociation (CAD) of these anions causes fragmentation reactions that include ring opening, E2 elimination, and decarbonylation. Mechanisms for these reactions are proposed, and these mechanisms are supported by study of partially deuterated analogs of 1 and 2.

  DOI：

  10.1080/07328309608005697
• 作为产物：
  描述：

  Methyl 3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranoside 在 吡啶 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 4.0h， 生成 4-O-benzoyl-3-O-benzyl-2,6-dideoxy-α-D-arabino-hexopyranose
  参考文献：
  名称：

  Photoremovable hydroxyl group protection. Use of the p-tolylsulfonyl protecting group in .beta.-disaccharide synthesis

  摘要：

  DOI：

  10.1021/jo00276a015

文献信息

• 10.1002/asia.200900640.
  作者：Tanaka, Hiroshi、Yamaguchi, Sho、Yoshizawa, Atsushi、Takagi, Motoki、Shinya, Kazuo、Takahashi, Takashi

  DOI：10.1002/asia.200900640.

  日期：——
• Negative-Ion Mass Spectrometry of Carbohydrates. A Mechanistic Study of the Fragmentation Reactions of Dideoxy Sugars
  作者：Roger W. Binkley、Edith R. Binkley、Shaoming Duan、Michael J. S. Tevesz、Witold Winnik

  DOI：10.1080/07328309608005697

  日期：1996.9

  Hydroxyl group deprotonation of the alpha and beta anomers of methyl 3-O-benzyl-2,6-dideoxy-D-arabino-hexopyranoside (1 and 2) occurs readily in the gas phase to produce the corresponding anions 3 and 4, respectively. Collisionally activated dissociation (CAD) of these anions causes fragmentation reactions that include ring opening, E2 elimination, and decarbonylation. Mechanisms for these reactions are proposed, and these mechanisms are supported by study of partially deuterated analogs of 1 and 2.
• Photoremovable hydroxyl group protection. Use of the p-tolylsulfonyl protecting group in .beta.-disaccharide synthesis
  作者：Roger W. Binkley、Dolores J. Koholic

  DOI：10.1021/jo00276a015

  日期：1989.7