(2R,3R,4S,5R,6R)-2-Hydroxymethyl-6-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-tetrahydro-pyran-3,4,5-triol | 287973-40-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6R)-2-Hydroxymethyl-6-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-tetrahydro-pyran-3,4,5-triol
• 英文别名: (2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-[4-[3-(trifluoromethyl)diazirin-3-yl]phenoxy]oxane-3,4,5-triol
• CAS: 287973-40-4
• 化学式: C₁₄H₁₅F₃N₂O₆
• 分子量: 364.278
• InChiKey: LCXCQRHELIUUNS-IIRVCBMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-2-Hydroxymethyl-6-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-tetrahydro-pyran-3,4,5-triol 在 galactose oxidase 、 phosphate buffer 、 catalase 作用下， 反应 1.0h， 生成 (2S,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-tetrahydro-pyran-2-carbaldehyde
  参考文献：
  名称：

  Syntheses and properties of photoactivatable sugar derivatives designed to probe the sugar-binding site of melibiose permease

  摘要：

  Three new photoreactive sugar analogues bearing an azido, a diazonium salt or a diazirine group as the photophore as well as a tritium atom were developed. Two of these new photoactivatable compounds gave excellent preliminary results, with a high affinity for the melibiose permease of Escherichia coli. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00180-3
• 作为产物：
  描述：

  Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-tetrahydro-pyran-3-yl ester 在 甲醇 、 sodium methylate 作用下， 反应 5.0h， 以90%的产率得到(2R,3R,4S,5R,6R)-2-Hydroxymethyl-6-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Syntheses and properties of photoactivatable sugar derivatives designed to probe the sugar-binding site of melibiose permease

  摘要：

  Three new photoreactive sugar analogues bearing an azido, a diazonium salt or a diazirine group as the photophore as well as a tritium atom were developed. Two of these new photoactivatable compounds gave excellent preliminary results, with a high affinity for the melibiose permease of Escherichia coli. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00180-3