2',2',2'-Trifluoroethyl 2,3,4-tri-O-acetyl-6-S-acetyl-β-D-glucopyranoside | 1412408-53-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2',2',2'-Trifluoroethyl 2,3,4-tri-O-acetyl-6-S-acetyl-β-D-glucopyranoside
• 英文别名: [(2S,3S,4S,5R,6R)-4,5-diacetyloxy-2-(acetylsulfanylmethyl)-6-(2,2,2-trifluoroethoxy)oxan-3-yl] acetate
• CAS: 1412408-53-7
• 化学式: C₁₆H₂₁F₃O₉S
• 分子量: 446.399
• InChiKey: GFUMENIUHDMDIT-UXXRCYHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2',2',2'-Trifluoroethyl 2,3,4-tri-O-acetyl-6-S-acetyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以71%的产率得到2',2',2'-trifluoroethyl 6-thio-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
• 作为产物：
  描述：

  2,2,2-Trifluoroethyl β-D-glucopyranoside 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 92.0h， 生成 2',2',2'-Trifluoroethyl 2,3,4-tri-O-acetyl-6-S-acetyl-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