(2S,3S,4R,5R)-2-trifluoroacetamido-5-methyl-piperidine-3,4-diol

• 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: (2S,3S,4R,5R)-2-trifluoroacetamido-5-methyl-piperidine-3,4-diol
• 英文别名: (2S)-2beta-(Trifluoroacetylamino)-5alpha-methylpiperidine-3alpha,4alpha-diol；N-[(2S,3S,4R,5R)-3,4-dihydroxy-5-methylpiperidin-2-yl]-2,2,2-trifluoroacetamide
• 化学式: C₈H₁₃F₃N₂O₃
• 分子量: 242.198
• InChiKey: RMHWFYGHKUFLAI-KAZBKCHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  81.6
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R)-2-trifluoroacetamido-5-methyl-piperidine-3,4-diol 在 citrate-phosphate buffer 作用下， 以 重水 为溶剂， 反应 48.0h， 生成 (4R,5R)-5-Methyl-piperidine-3,3,4-triol 、 (2S,3R,4R,5R)-5-Methyl-piperidine-2,3,4-triol
  参考文献：
  名称：

  Glycosidase inhibitors of gem-diamine 1-N-iminosugars structures in media of enzyme assays

  摘要：

  The relationships between structures and inhibitory activities of glycosidase inhibitors of gem-diamine 1-N-iminosugars in media of enzyme assays have been investigated. It has been proved that gem-diamine 1-N-iminosugar smoothly undergoes a structural change to a hydrated ketone or its derivative via a hemiaminal in the media (pH 5.0-6.3), and that the products generated in the media as well as the parent gem-diamine 1-N-iminosugars potently inhibit glycosidases. (C) 2001 Elsevier Science Ltd. Al rights reserved.

  DOI：

  10.1016/s0968-0896(00)00330-8

文献信息

• 2-N-SUBSTITUTED OR UNSUBSTITUTED-2-AMINO-5-METHYLPIPERIDINE-3,4-DIOLS AND PROCESSES FOR THE PREPARATION THEREOF
  申请人：ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI

  公开号：EP1156038A1

  公开（公告）日：2001-11-21

  This invention relates to (2R,3S,4R,5R)-2-amino-5-methylpiperidine-3,4-diol or a (2S,3S,4R,5R)-2-N-substituted-2-amino-5-methylpiperidine-3,4-diol represented by the general formula (I): wherein R1 and R2 each are a hydrogen atom, or R1 is a hydrogen atom and R2 is a lower alkanoyl group or a lower ω-trihaloalkanoyl group, or R1 and R2 together denote phthaloyl group, and a pharmaceutically acceptable salt thereof. Said compound can be prepared from a (2S,3S,4R)-5-N-protected-2,3,4-O-tri-protected-5-aminopentane-1,2,3,4-tetraol by multi-steps of reactions.

  本发明涉及通式(I)代表的(2R,3S,4R,5R)-2-氨基-5-甲基哌啶-3,4-二醇或(2S,3S,4R,5R)-2-N-取代的-2-氨基-5-甲基哌啶-3,4-二醇： 其中 R1 和 R2 各为氢原子，或 R1 为氢原子，R2 为低级烷酰基或低级ω-三卤代烷酰基，或 R1 和 R2 共同表示邻苯二甲酰基团，及其药学上可接受的盐。 所述化合物可由(2S,3S,4R)-5-N-保护-2,3,4-O-三保护-5-氨基戊烷-1,2,3,4-四醇通过多步反应制备。
• US6610709B1
  申请人：——

  公开号：US6610709B1

  公开（公告）日：2003-08-26
• Glycosidase inhibitors of gem-diamine 1-N-iminosugars structures in media of enzyme assays
  作者：K Kondo

  DOI：10.1016/s0968-0896(00)00330-8

  日期：2001.5

  The relationships between structures and inhibitory activities of glycosidase inhibitors of gem-diamine 1-N-iminosugars in media of enzyme assays have been investigated. It has been proved that gem-diamine 1-N-iminosugar smoothly undergoes a structural change to a hydrated ketone or its derivative via a hemiaminal in the media (pH 5.0-6.3), and that the products generated in the media as well as the parent gem-diamine 1-N-iminosugars potently inhibit glycosidases. (C) 2001 Elsevier Science Ltd. Al rights reserved.