2,3,4,6-tetra-O-acetyl-β-D-[glucose-[(13)C6]]-glucopyranosyl-4-methylthiobutylthiohydroximate | 1173694-49-9

• 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: 2,3,4,6-tetra-O-acetyl-β-D-[glucose-[(13)C6]]-glucopyranosyl-4-methylthiobutylthiohydroximate
• CAS: 1173694-49-9
• 化学式: C₂₀H₃₁NO₁₀S₂
• 分子量: 515.533
• InChiKey: RTCNCWURDIKXON-SHDNVTFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  33.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  147.02
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-[glucose-[(13)C6]]-glucopyranosyl-4-methylthiobutylthiohydroximate 在 吡啶 、 三氧化硫吡啶 、 potassium hydrogencarbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.5h， 以77%的产率得到2,3,4,6-tetra-O-acetyl-β-D-[glucose-[(13)C6]]glucopyranosyl-4-methythiobutyl-O-sulfate thiohydroximate potassium salt
  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-tetra-O-acetyl-1-thio-β-D-[(13)C6]-glucopyranose 、 N-hydroxy-5-methylsulfanylpentanimidoyl chloride 在 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 为溶剂， 以0.456 g的产率得到2,3,4,6-tetra-O-acetyl-β-D-[glucose-[(13)C6]]-glucopyranosyl-4-methylthiobutylthiohydroximate
  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