2,5-二(羟基甲基)-3,4-吡咯烷二醇 | 132295-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 2,5-二(羟基甲基)-3,4-吡咯烷二醇
• 英文名称: 2,5-anhydro-2,5-imino-D-glucitol
• 英文别名: 2,5-dideoxy-2,5-imino-D-glucitol；(2S,3R,4R,5R)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol；(2R,3R,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)pyrrolidine；(2R,5S)-dihydroxymethyl-(3R,4R)-dihydroxypyrrolidine；(2R,3R,4R,5S)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol
• CAS: 132295-44-4
• 化学式: C₆H₁₃NO₄
• 分子量: 163.174
• InChiKey: PFYHYHZGDNWFIF-JGWLITMVSA-N

物化性质

• 熔点：
  139-142.5°C
• 溶解度：
  甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-二(羟基甲基)-3,4-吡咯烷二醇 在 镍 咪唑 、 sodium azide 、 高氯酸 、 氢气 、 碘 、 溶剂黄146 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 94.0h， 生成
  参考文献：
  名称：

  Ethambutol–sugar hybrids as potential inhibitors of mycobacterial cell-wall biosynthesis

  摘要：

  Ethambutol is an established front-line agent for the treatment of tuberculosis, and is also active against Mycobacterium avium infection. However, this agent exhibits toxicity, and is considered to have low potency. The action of ethambutol on the mycobacterial cell wall, particularly the arabinan, and comparison of the structure of ethambutol with several of the cell-wall saccharides, suggested that ethambutol-saccharide hybrids might lead to agents with a more selective mechanism of action. To this end, eight ethambutol-saccharide hybrids were synthesized and screened against M. tuberculosis and several clinical isolates of M. avium. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00069-5
• 作为产物：
  描述：

  5-酮果糖 在 palladium dihydroxide 氢气 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 生成 2,5-二(羟基甲基)-3,4-吡咯烷二醇
  参考文献：
  名称：

  一步法从二羰基糖中制得吡咯烷和哌啶氨基糖。1-deoxynojirimycin的简捷合成

  摘要：

  二羰基糖是通过双重还原胺化反应（NaCNBH 3，MeOH）进行立体选择性合成羟基化哌啶和吡咯烷的便​​利底物。使用这种策略，由5-酮-D-果糖（2，可商购）和5-酮-D-葡萄糖（2，5-脱水亚氨基-D-葡萄糖醇（1）和1-脱氧野rim霉素（3））制备。4）。

  DOI：

  10.1016/s0040-4039(00)97169-7

文献信息

• Iminocyclitol inhibitors of hexoaminidase and glycosidase
  申请人：The Scripps Research Institute

  公开号：US06774140B1

  公开（公告）日：2004-08-10

  Designed iminocylitols that have potent inhibition activity with respect to hexominidases and glycosides are disclosed.

  披露了设计的亚氨基糖醇，它们对己糖苷酶和苷具有强大的抑制活性。
• Antibody-catalysed glycosyl transfer reactions from in vitro immunization
  作者：Jaehoon Yu、So Young Choi、Sungsoo Lee、Hansuh Mun、Hokoon Park、Hyun Joo Yoon、Sunjoo Jeong、Peter G. Schultz

  DOI：10.1039/a704885h

  日期：——

  In vitro immunization using a 5-membered ring iminocyclitol afforded antibodies that catalyse the hydrolysis of p-nitrophenyl glucopyranoside and p-nitrophenyl galactopyranoside with rate enhancements (kcat/kuncat) of greater than 104.

  使用五元环亚胺环醇在体外进行免疫，获得了能够催化对硝基苯基吡喃葡萄糖苷和对硝基苯基吡喃半乳糖苷水解的抗体，其速率增益（kcat/kuncat）超过10,000倍。
• HIV protease inhibitors
  申请人：Wong Chi-Huey

  公开号：US06900238B1

  公开（公告）日：2005-05-31

  Combinatorial libraries of HIV and FIV protease inhibitors are characterized by α-keto amide or hydroxyethylamine core structures flanked by on one side by substituted pyrrolidines, piperidines, or azasugars and on the other side by phenylalanine, tyrosine, or substituted tyrosines. The libraries are synthesized via a one step coupling reaction. Highly efficacious drug candidates are identified by screening the libraries for binding and inhibitory activity against both HIV and FIV protease. Drug candidates displaying clinically useful activity against both HIV and FIV protease are identified as being potentially resistive against a loss of inhibitory activity due to development of resistant strains of HIV.

  HIV和FIV蛋白酶抑制剂的组合库以α-酮酰胺或羟乙基胺核心结构为特征，一侧为取代吡咯烷、哌啶或氮代糖，另一侧为苯丙氨酸、酪氨酸或取代酪氨酸。这些库是通过一步偶联反应合成的。通过筛选这些库，识别出对HIV和FIV蛋白酶的结合和抑制活性高效的药物候选化合物。对HIV和FIV蛋白酶都显示出临床有用活性的药物候选化合物被确定为潜在对抗由于HIV耐药株的发展而导致的抑制活性丧失。
• Synthesis of (+)-DGDP and (−)-7-epialexine
  作者：Timothy J. Donohoe、Matthew D. Cheeseman、Timothy J. C. O'Riordan、Jessica A. Kershaw

  DOI：10.1039/b815332a

  日期：——

  The partial reduction of electron deficient pyrroles is an extremely versatile method that allows us to prepare substituted pyrrolidines and pyrrolizidines with trans-diol stereochemistry on the five membered ring.

  电子缺乏吡咯的部分还原是一种极为多功能的方法，使我们能够合成具有反式二醇立体化学的取代吡咯烷和吡咯啉。
• Homologated aza analogs of arabinose as antimycobacterial agents
  作者：Joseph A. Maddry、Namita Bansal、Luiz E. Bermudez、Robert N. Comber、Ian M. Orme、William J. Suling、Larry N. Wilson、Robert C. Reynolds

  DOI：10.1016/s0960-894x(98)00017-1

  日期：1998.2

  A series of hydrolytically-stable aza analogs of arabinofuranose was prepared and evaluated against Mycobacterium tuberculosis and M. avium. The compounds were designed to mimic the putative arabinose donor involved in biogenesis of the essential cell wall polysaccharide, arabinogalactan. Though most compounds displayed little activity in cell culture, one compound showed significant activity in infected

  制备了一系列阿拉伯呋喃糖水解稳定的氮杂类似物，并针对结核分枝杆菌和鸟分枝杆菌进行了评估。设计这些化合物以模拟参与必需细胞壁多糖阿拉伯半乳聚糖的生物发生的推定的阿拉伯糖供体。尽管大多数化合物在细胞培养中显示很少的活性，但一种化合物在感染的巨噬细胞模型中显示了显着的活性。