5-azido-5-deoxy-6-O-(6'-hydroxy)hexyl-D-fructose | 315190-58-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-azido-5-deoxy-6-O-(6'-hydroxy)hexyl-D-fructose
• 英文别名: (3S,4R,5R)-5-azido-1,3,4-trihydroxy-6-(6-hydroxyhexoxy)hexan-2-one
• CAS: 315190-58-0
• 化学式: C₁₂H₂₃N₃O₆
• 分子量: 305.331
• InChiKey: UQPQXTCMRAZXKQ-YUSALJHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  122
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-azido-5-deoxy-6-O-(6'-hydroxy)hexyl-D-fructose 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以63%的产率得到2,5-dideoxy-1-O-(6'-hydroxyhexyl)-2,5-imino-D-mannitol
  参考文献：
  名称：

  Biologically Active 1-Aminodeoxy and 1-O-Alkyl Derivatives of The Powerful D-Glucosidase Inhibitor 2,5-Dideoxy-2,5-Imino-D-Mannitol

  摘要：

  By an Amadori rearrangement of easily available 5-azido-5-deoxy-D-glucofuranose with dibenzylamine and subsequent catalytic hydrogenation of the resulting 5-azido-1-(N,N-dibenzyl)amino-1,5-dideoxy-D-fructopyranose 1-amino-1,2,5-trideoxy-2,5-imino-D-mannitol was obtained in only two steps and in excellent overall yield. Likewise, other amines were employed to introduce extended side chains ultimately suitable for attachment of the inhibitor to solid supports. The reported rearrangement reaction is a high yielding, convenient and apparently general entry to I-amino deoxyketopyranoses modified at C-5, facilitated by the ring enlargement of the aldofuranose to the ketopyranose as an additional driving force. A range of selected chain extended analogues was prepared by acylation of N-1. Inhibitors obtained exhibit K-i-values with D-glucosidases in the micromolar range. Interestingly, 1-N-acylation resulted in superior inhibitory activities, as did the addition of a hexyl chain.

  DOI：

  10.1080/07328300008544129
• 作为产物：
  描述：

  5-azido-5-deoxy-6-O-(6'-hydroxy)hexyl-D-glucofuranose 在 EC 5.3.1.5 、 glucose isomerase Sweetzyme T 、 magnesium sulfate 作用下， 以 水 为溶剂， 反应 12.0h， 以23.7%的产率得到5-azido-5-deoxy-6-O-(6'-hydroxy)hexyl-D-fructose
  参考文献：
  名称：

  Biologically Active 1-Aminodeoxy and 1-O-Alkyl Derivatives of The Powerful D-Glucosidase Inhibitor 2,5-Dideoxy-2,5-Imino-D-Mannitol

  摘要：

  By an Amadori rearrangement of easily available 5-azido-5-deoxy-D-glucofuranose with dibenzylamine and subsequent catalytic hydrogenation of the resulting 5-azido-1-(N,N-dibenzyl)amino-1,5-dideoxy-D-fructopyranose 1-amino-1,2,5-trideoxy-2,5-imino-D-mannitol was obtained in only two steps and in excellent overall yield. Likewise, other amines were employed to introduce extended side chains ultimately suitable for attachment of the inhibitor to solid supports. The reported rearrangement reaction is a high yielding, convenient and apparently general entry to I-amino deoxyketopyranoses modified at C-5, facilitated by the ring enlargement of the aldofuranose to the ketopyranose as an additional driving force. A range of selected chain extended analogues was prepared by acylation of N-1. Inhibitors obtained exhibit K-i-values with D-glucosidases in the micromolar range. Interestingly, 1-N-acylation resulted in superior inhibitory activities, as did the addition of a hexyl chain.

  DOI：

  10.1080/07328300008544129