2,2,2-Trifluoroethyl α-D-glucopyranoside | 29074-00-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,2-Trifluoroethyl α-D-glucopyranoside
• 英文别名: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(2,2,2-trifluoroethoxy)oxane-3,4,5-triol
• CAS: 29074-00-8
• 化学式: C₈H₁₃F₃O₆
• 分子量: 262.183
• InChiKey: CTODQMNMLKVZIB-ZFYZTMLRSA-N

物化性质

• 沸点：
  398.9±42.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  D-葡萄糖 、 2,2,2-三氟乙醇 在 乙酰氯 作用下， 反应 0.17h， 以8%的产率得到2,2,2-Trifluoroethyl β-D-glucopyranoside
  参考文献：
  名称：

  2,2,2-Trifluoroethyl 6-thio-β-d-glucopyranoside as a selective tag for cysteines in proteins

  摘要：

  A synthetic route to a trifluoromethyl and thiol containing glucose derivative (2,2,2-trifluoroethyl 6-thio-beta-D-glucopyranoside) is presented, which is based on microwave-assisted Fischer glycosylation under increased pressure. This water-soluble, neutral thiol-compound can be used to selectively introduce a fluorine probe for F-19 NMR spectroscopy on cysteines in proteins. It can be attached under mild conditions in an aqueous environment without the risk of denaturing the protein. This tag has been applied to determine the redox-state of two cysteine residues in a bacterial transcription activator. Qualitative information about the solvent accessibility can be obtained from F-19 solvent PREs. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.08.010

文献信息

• Solvolysis of D-glucopyranosyl derivatives in mixtures of ethanol and 2,2,2-trifluoroethanol
  作者：Michael L. Sinnott、William P. Jencks

  DOI：10.1021/ja00526a043

  日期：1980.3
• 2,2,2-Trifluoroethyl 6-thio-β-d-glucopyranoside as a selective tag for cysteines in proteins
  作者：Richard F.G. Fröhlich、Evelyne Schrank、Klaus Zangger

  DOI：10.1016/j.carres.2012.08.010

  日期：2012.11

  A synthetic route to a trifluoromethyl and thiol containing glucose derivative (2,2,2-trifluoroethyl 6-thio-beta-D-glucopyranoside) is presented, which is based on microwave-assisted Fischer glycosylation under increased pressure. This water-soluble, neutral thiol-compound can be used to selectively introduce a fluorine probe for F-19 NMR spectroscopy on cysteines in proteins. It can be attached under mild conditions in an aqueous environment without the risk of denaturing the protein. This tag has been applied to determine the redox-state of two cysteine residues in a bacterial transcription activator. Qualitative information about the solvent accessibility can be obtained from F-19 solvent PREs. (C) 2012 Elsevier Ltd. All rights reserved.