S-(2,3,4,6-tetra-o-acetyl-β-D-glucopyranosyl) (Z)-2-phenylethanethiohydroximate | 156258-43-4

• 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: S-(2,3,4,6-tetra-o-acetyl-β-D-glucopyranosyl) (Z)-2-phenylethanethiohydroximate
• 英文别名: S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)phenylacetothiohydroxamate
• CAS: 156258-43-4
• 化学式: C₂₂H₂₇NO₁₀S
• 分子量: 497.523
• InChiKey: JRJCZQRDQFFFGS-LYECDSABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  147.02
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  S-(2,3,4,6-tetra-o-acetyl-β-D-glucopyranosyl) (Z)-2-phenylethanethiohydroximate 在 三氧化硫吡啶 、 potassium hydrogencarbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 20.5h， 以83%的产率得到potassium 2,3,4,6-tetra-O-acetylglucotropaeolin
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of aromatic glucosinolates

  摘要：

  Aromatic GLs are important members of the glucosinolate family of compounds because of their potential biological activity and medicinal properties. This study has shown success in the high yielding synthesis of some important aromatic GLs as well as the results of testing for anti-inflammatory properties of the synthetic GLs. 3,4-Dimethoxyphenylglucosinolate was found to be the most active anti-inflammatory of the seven glucosinolates assayed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.049
• 作为产物：
  描述：

  苯乙醛肟 在 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 S-(2,3,4,6-tetra-o-acetyl-β-D-glucopyranosyl) (Z)-2-phenylethanethiohydroximate
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of aromatic glucosinolates

  摘要：

  Aromatic GLs are important members of the glucosinolate family of compounds because of their potential biological activity and medicinal properties. This study has shown success in the high yielding synthesis of some important aromatic GLs as well as the results of testing for anti-inflammatory properties of the synthetic GLs. 3,4-Dimethoxyphenylglucosinolate was found to be the most active anti-inflammatory of the seven glucosinolates assayed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.049

文献信息

• Glucosinolate Synthesis: a Hydroxamic Acid Approach
  作者：Deimante Cerniauskaite、Jolanta Rousseau、Algirdas Sackus、Patrick Rollin、Arnaud Tatibouët

  DOI：10.1002/ejoc.201001438

  日期：2011.4

  the thiohydroximate function allows an alternative synthetic pathway to glucosinolates. O-Silylated hydroxamic acids were prepared and were then activated with triflic anhydride to generate transient nitrile oxides to be condensed with ethanethiol. The procedure was further applied to the synthesis of naturally occurring glucosinolates.

  一种用于访问硫羟肟酸功能的新方法为硫代葡萄糖苷提供了另一种合成途径。制备了 O-甲硅烷基化异羟肟酸，然后用三氟甲磺酸酐活化以生成瞬态腈氧化物以与乙硫醇缩合。该程序进一步应用于合成天然存在的硫代葡萄糖苷。
• Synthesis of an artificial phosphate bio-isostere of glucotropaeolin
  作者：Saïd Lazar、Patrick Rollin

  DOI：10.1016/s0040-4039(00)76788-8

  日期：1994.4

  A synthetic sequence was devised to produce phospho-glucotropaeolin 6, the first representative of phosphate bio-isosteres of naturally-occurring glucosinolates with a view to enzymatic studies.