(3R,4R,5R)-3,4,5-trihydroxypiperidine-3-carboxylic acid | 1207672-54-5

• 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: (3R,4R,5R)-3,4,5-trihydroxypiperidine-3-carboxylic acid
• 英文别名: 2-C-carboxylic acid-1,5-dideoxy-1,5-imino-D-arabinitol
• CAS: 1207672-54-5
• 化学式: C₆H₁₁NO₅
• 分子量: 177.157
• InChiKey: CPYMDLPWOUXULD-ZMIZWQJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-azido-5-deoxy-2-C-hydroxymethyl-2,3-O-isopropylidene-2'-C-trifluoromethanesulfonyl-D-ribono-1,4-lactone 在 palladium 10% on activated carbon 、 水 、 氢气 、 三氟乙酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 41.0h， 生成 (3R,4R,5R)-3,4,5-trihydroxypiperidine-3-carboxylic acid
  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

• Treatment of energy utilization disease
  申请人：Vida Pharma Limited

  公开号：US10842784B2

  公开（公告）日：2020-11-24

  Described are compositions comprising imino sugar acids for the treatment of energy utilization disease (e.g. metabolic syndrome, including any disease or disorder associated therewith, for example central obesity, elevated levels of triglycerides and diabetes, including type 1 diabetes, type 2 diabetes and insulin resistance), processes for producing said compositions from various plant sources, together with various products, compounds, compositions, medical uses and methods based thereon.

  所描述的是包含亚氨基糖酸的组合物，用于治疗能量利用疾病（例如代谢综合征，包括与之相关的任何疾病或紊乱，例如中心性肥胖、甘油三酯水平升高和糖尿病，包括 1 型糖尿病、2 型糖尿病和胰岛素抵抗）；从各种植物来源生产所述组合物的工艺，以及基于此的各种产品、化合物、组合物、医疗用途和方法。
• Treatment of Energy Utilization Disease
  申请人：Nash Robert James

  公开号：US20110015226A1

  公开（公告）日：2011-01-20

  Described are compositions comprising imino sugar acids for the treatment of energy utilization disease (e.g. metabolic syndrome, including any disease or disorder associated therewith, for example central obesity, elevated levels of triglycerides and diabetes, including type 1 diabetes, type 2 diabetes and insulin resistance), processes for producing said compositions from various plant sources, together with various products, compounds, compositions, medical uses and methods based thereon.
• COMPOUNDS FOR THE TREATMENT OF FLAVIVIRAL INFECTIONS
  申请人：De Moor Olivier

  公开号：US20110195929A1

  公开（公告）日：2011-08-11

  Described are various compounds and methods for the treatment of flaviviral infections. In particular, alkaloids and imino sugars in arabinose and/or lyxose stereochemical configuration with antiflaviviral activity are described.
• TREATMENT OF ENERGY UTILIZATION DISEASE
  申请人：Summit Corporation PLC

  公开号：US20160151341A1

  公开（公告）日：2016-06-02

  Described are compositions comprising imino sugar acids for the treatment of energy utilization disease (e.g. metabolic syndrome, including any disease or disorder associated therewith, for example central obesity, elevated levels of triglycerides and diabetes, including type 1 diabetes, type 2 diabetes and insulin resistance), processes for producing said compositions from various plant sources, together with various products, compounds, compositions, medical uses and methods based thereon.
• 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.