2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-1-naphthylmethyl thiohydroximate | 340960-74-9

• 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-glucopyranosyl-1-naphthylmethyl thiohydroximate
• CAS: 340960-74-9
• 化学式: C₂₆H₂₉NO₁₀S
• 分子量: 547.583
• InChiKey: MKUZSSKKURSYBJ-ZGLCYIBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-1-naphthylmethyl thiohydroximate 在 吡啶 、 氯磺酸 、 potassium methanolate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 potassium;[(Z)-[2-naphthalen-1-yl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylethylidene]amino] sulfate
  参考文献：
  名称：

  Synthesis, analysis and rearrangement of novel unnatural glucosinolates

  摘要：

  As part of a structure activity study to examine the interaction of glucosinolates with leaf surfaces,a number of glucosinolates were synthesised bearing novel side chain functionalities. These included 7-carboxyheptyl, heptyl, and naphthyl side chains. For the carboxyheptyl glucosinolate, a novel intramolecular rearrangement reaction was observed during the final deprotection step, which generated an ester attached to the C-3 of glucose. Studies by H-1 NMR spectroscopy showed that the hydrophobic side chain associated with one face of the glucose ring and it was proposed that this was the driving force for the rearrangement. Similar hydrophobic interactions were also observed between the heptyl and naphthyl side chains and the glucose. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00308-6
• 作为产物：
  描述：

  1-naphthylacetaldoxime 在 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 氯仿 为溶剂， 反应 4.0h， 生成 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-1-naphthylmethyl thiohydroximate
  参考文献：
  名称：

  Synthesis, analysis and rearrangement of novel unnatural glucosinolates

  摘要：

  As part of a structure activity study to examine the interaction of glucosinolates with leaf surfaces,a number of glucosinolates were synthesised bearing novel side chain functionalities. These included 7-carboxyheptyl, heptyl, and naphthyl side chains. For the carboxyheptyl glucosinolate, a novel intramolecular rearrangement reaction was observed during the final deprotection step, which generated an ester attached to the C-3 of glucose. Studies by H-1 NMR spectroscopy showed that the hydrophobic side chain associated with one face of the glucose ring and it was proposed that this was the driving force for the rearrangement. Similar hydrophobic interactions were also observed between the heptyl and naphthyl side chains and the glucose. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00308-6