2,3,4,6-tetra-O-acetyl-β-D-[(13)C6]glucopyranosyl isothiouronium bromide | 1173694-37-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-acetyl-β-D-[(13)C6]glucopyranosyl isothiouronium bromide
• CAS: 1173694-37-5
• 化学式: BrH*C₁₅H₂₂N₂O₉S
• 分子量: 493.26
• InChiKey: QNVDHERXTIAGPT-QPWNTOCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.27
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  164.3
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-[(13)C6]glucopyranosyl isothiouronium bromide 在 potassium disulphite 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以93%的产率得到2,3,4,6-tetra-O-acetyl-1-thio-β-D-[(13)C6]-glucopyranose
  参考文献：
  名称：

  The synthesis of novel hexa-13C-labelled glucosinolates from [13C6]-d-glucose

  摘要：

  An isotopically labelled building block, 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-[C-13(6)]glucopyranose (4), is obtained from the commercially available [C-13(6)]-D-glucose. This hexa-C-13-labelled thioglucose can be employed to make any glucosinolate (8) for use as an internal standard for isotopic dilution LCMS analysis. Herein three typical glucosinolates in their hexa-C-13-labelled form: [glucose-C-13(6)]gluconasturtiin, [glucose-C-13(6)]sinigrin and [glucose-C-13(6)]glucoerucin are synthesised by coupling the isotopically labelled thioglucose (4) with the corresponding hydroximoyl chlorides followed by sulfation with pyridine sulfur trioxide and deacetylation with a catalytic amount of potassium methoxide, respectively. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.043
• 作为产物：
  描述：

  2,3,4,6-tetraacetyl-1-bromo-α-D-[¹³C₆]-glucopyranoside 、 硫脲 以 丙酮 为溶剂， 反应 0.5h， 以80%的产率得到2,3,4,6-tetra-O-acetyl-β-D-[(13)C6]glucopyranosyl isothiouronium bromide
  参考文献：
  名称：

  The synthesis of novel hexa-13C-labelled glucosinolates from [13C6]-d-glucose

  摘要：

  An isotopically labelled building block, 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-[C-13(6)]glucopyranose (4), is obtained from the commercially available [C-13(6)]-D-glucose. This hexa-C-13-labelled thioglucose can be employed to make any glucosinolate (8) for use as an internal standard for isotopic dilution LCMS analysis. Herein three typical glucosinolates in their hexa-C-13-labelled form: [glucose-C-13(6)]gluconasturtiin, [glucose-C-13(6)]sinigrin and [glucose-C-13(6)]glucoerucin are synthesised by coupling the isotopically labelled thioglucose (4) with the corresponding hydroximoyl chlorides followed by sulfation with pyridine sulfur trioxide and deacetylation with a catalytic amount of potassium methoxide, respectively. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.043