(3aR,7R,7aR)-7-hydroxy-3a-(hydroxymethyl)-2,2-dimethyl-5,6,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyridin-4-one | 1207675-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3aR,7R,7aR)-7-hydroxy-3a-(hydroxymethyl)-2,2-dimethyl-5,6,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyridin-4-one
• CAS: 1207675-29-3
• 化学式: C₉H₁₅NO₅
• 分子量: 217.222
• InChiKey: CJSYFMXCKWKAHJ-HCVRKRLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,7R,7aR)-7-hydroxy-3a-(hydroxymethyl)-2,2-dimethyl-5,6,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyridin-4-one 在 水 、 三氟乙酸 作用下， 反应 16.0h， 以100%的产率得到5-amino-5-deoxy-2-C-hydroxymethyl-D-ribono-1,5-lactam
  参考文献：
  名称：

  Synthesis of three branched iminosugars [(3R,4R,5S)-3-(hydroxymethyl)piperidine-3,4,5-triol, (3R,4R,5R)-3-(hydroxymethyl)piperidine-3,4,5-triol and (3S,4R,5R)-3-(hydroxymethyl)piperidine-3,4,5-triol] and a branched trihydroxynipecotic acid [(3R,4R,5R)-3,4,5-trihydroxypiperidine-3-carboxylic acid] from sugar lactones with a carbon substituent at C-2

  摘要：

  Homochiral piperidines containing a quaternary carbon branch at C-2 of the piperidine ring may be made from readily available carbohydrate lactones containing a branched 2-C-hydroxymethyl substituent. This gives an easy access to the branched iininosugars. In particular a trihydroxypipecolic acid analogue, (3R,4R,5R)-3,4,5-trihydroxypiperidine-3-carboxylic acid, has been synthesised efficiently from the starting material D-ribose and (35,4R,5S)-3-(hydroxymethyl)piperidine-3,4,5-triol was found to be a specific inhibitor of alpha-D-glucosidase from Bacillus Stearothermophilus with an IC50 value of 93 mu M. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.007
• 作为产物：
  描述：

  5-azido-5-deoxy-2-C-hydroxymethyl-2,3-O-isopropylidene-ribono-1,4-lactone 在 氢气 、 钯 作用下， 以 1,4-二氧六环 为溶剂， 反应 17.5h， 以100%的产率得到(3aR,7R,7aR)-7-hydroxy-3a-(hydroxymethyl)-2,2-dimethyl-5,6,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyridin-4-one
  参考文献：
  名称：

  Synthesis of three branched iminosugars [(3R,4R,5S)-3-(hydroxymethyl)piperidine-3,4,5-triol, (3R,4R,5R)-3-(hydroxymethyl)piperidine-3,4,5-triol and (3S,4R,5R)-3-(hydroxymethyl)piperidine-3,4,5-triol] and a branched trihydroxynipecotic acid [(3R,4R,5R)-3,4,5-trihydroxypiperidine-3-carboxylic acid] from sugar lactones with a carbon substituent at C-2

  摘要：

  Homochiral piperidines containing a quaternary carbon branch at C-2 of the piperidine ring may be made from readily available carbohydrate lactones containing a branched 2-C-hydroxymethyl substituent. This gives an easy access to the branched iininosugars. In particular a trihydroxypipecolic acid analogue, (3R,4R,5R)-3,4,5-trihydroxypiperidine-3-carboxylic acid, has been synthesised efficiently from the starting material D-ribose and (35,4R,5S)-3-(hydroxymethyl)piperidine-3,4,5-triol was found to be a specific inhibitor of alpha-D-glucosidase from Bacillus Stearothermophilus with an IC50 value of 93 mu M. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.007

文献信息

• Synthesis of three branched iminosugars [(3R,4R,5S)-3-(hydroxymethyl)piperidine-3,4,5-triol, (3R,4R,5R)-3-(hydroxymethyl)piperidine-3,4,5-triol and (3S,4R,5R)-3-(hydroxymethyl)piperidine-3,4,5-triol] and a branched trihydroxynipecotic acid [(3R,4R,5R)-3,4,5-trihydroxypiperidine-3-carboxylic acid] from sugar lactones with a carbon substituent at C-2
  作者：Michela I. Simone、Raquel G. Soengas、Sarah F. Jenkinson、Emma L. Evinson、Robert J. Nash、George W.J. Fleet

  DOI：10.1016/j.tetasy.2012.03.007

  日期：2012.3

  Homochiral piperidines containing a quaternary carbon branch at C-2 of the piperidine ring may be made from readily available carbohydrate lactones containing a branched 2-C-hydroxymethyl substituent. This gives an easy access to the branched iininosugars. In particular a trihydroxypipecolic acid analogue, (3R,4R,5R)-3,4,5-trihydroxypiperidine-3-carboxylic acid, has been synthesised efficiently from the starting material D-ribose and (35,4R,5S)-3-(hydroxymethyl)piperidine-3,4,5-triol was found to be a specific inhibitor of alpha-D-glucosidase from Bacillus Stearothermophilus with an IC50 value of 93 mu M. (C) 2012 Elsevier Ltd. All rights reserved.