2,3,4,6-tetra-O-acetyl-1-S-(Z)-benzhydroximoyl-1-thio-β-D-glucopyranose | 150852-15-6

• 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-1-S-(Z)-benzhydroximoyl-1-thio-β-D-glucopyranose
• 英文别名: S-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl phenylthiohydroxamate；S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)phenylthiohydroxamate；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(Z)-N-hydroxy-C-phenylcarbonimidoyl]sulfanyloxan-2-yl]methyl acetate
• CAS: 150852-15-6
• 化学式: C₂₁H₂₅NO₁₀S
• 分子量: 483.496
• InChiKey: JXNITLIEBGOJMJ-ZQGTYELJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  172
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-1-S-(Z)-benzhydroximoyl-1-thio-β-D-glucopyranose 在 氯磺酸 、 氨 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 ammonium β-D-glucopyranosyl phenylthiohydroxamic N-sulfate
  参考文献：
  名称：

  Synthesis of [2,3,4,5,6-2H5]phenyl glucosinolate

  摘要：

  从市售的[2,3,4,5,6-2H5]苯甲酸开始，合成了[2,3,4,5,6-2H5]苯基葡糖苷酸。在负离子电喷雾离子化质谱条件下，该化合物在 m/z 399 处出现峰值。由于该 m/z 值无法从天然葡萄糖苷酸盐的离子中获得，因此本文报告的[2,3,4,5,6-2H5]苯基葡萄糖苷酸盐可用作负离子质谱（MS）和液相色谱（LC）/质谱技术定量葡萄糖苷酸盐的内标。Copyright © 2007 John Wiley & Sons, Ltd. All Rights Reserved.

  DOI：

  10.1002/jlcr.1407
• 作为产物：
  描述：

  苯甲醛肟 在 吡啶 、 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 氯仿 为溶剂， 反应 3.0h， 生成 2,3,4,6-tetra-O-acetyl-1-S-(Z)-benzhydroximoyl-1-thio-β-D-glucopyranose
  参考文献：
  名称：

  (Z)-Stereospecific Addition of Glycosylmercaptans on Nitrilium Betaines.¹Synthesis of 1-S-Glucopyranosyl Arylthiohydroximates

  摘要：

  With a view to selecting new internal standards for HPLC analysis of glucosinolates, the synthesis of artificial desulfoglucosinolates 5 was carried out.

  DOI：

  10.1080/00397919408011744

文献信息

• Collision-induced dissociation mass spectra of glucosinolate anions
  作者：Jason B. Bialecki、Josef Ruzicka、Carl S. Weisbecker、Meena Haribal、Athula B. Attygalle

  DOI：10.1002/jms.1711

  日期：2010.3

  for the thioglucose anion, which further dissociates via an ion/neutral complex to give two peaks at m/z 75 and 119. The other product ions observed at m/z 80, 96 and 97 are characteristic for the sulfate moiety. The peaks at m/z 259 and 275 have been attributed previously to glucose 1-sulfate anion and 1-thioglucose 2-sulfate anion, respectively. However, based on our tandem mass spectrometric experiments

  在负离子模式下研究了不同取代的芥子油苷的碰撞诱导解离（CID）质谱。从数个芥子油苷及其同位素（（34）S和（2）H）获得的数据表明，观察到的许多峰与取代基的性质无关。例如，所有研究过的芥子油苷阴离子片段都会在m / z 195处观察到硫代葡萄糖阴离子的产物离子，该硫离子会通过离子/中性络合物进一步解离，从而在m / z 75和119处出现两个峰。观察到的其他产物离子m / z为80、96和97的硫酸盐部分是特征性的。先前分别将m / z 259和275处的峰归因于葡萄糖1硫酸根阴离子和1-硫葡萄糖2硫酸根阴离子。但是，根据我们的串联质谱实验，我们建议在m / z 275处的峰代表葡萄糖1-硫代硫酸根阴离子。除常见峰外，芥子油酸苯基酯（β-D-葡糖醛糖，1-硫代-，1- [N-（磺氧基）苯甲酰亚胺）的光谱还显示出C（m / z 152）处的取代基特定峰6）H（5）-C（= NOH）S（-），
• Synthesis, structure and enzymatic evaluation of new spiro oxathiazole sugar derivatives
  作者：Jean-Pierre Praly、René Faure、Benoît Joseph、Laszlo Kiss、Patrick Rollin

  DOI：10.1016/s0040-4020(01)89686-1

  日期：——

  On treatment with N-bromosuccinimide under irradiation in refluxing carbon tetrachloride, 2,3,4,6-tetra-O-acetyl-1-S-(Z)-benzhydroximoyl-1-thio-D-glucopyranose 1 and various analogs yielded new spiro anomericoxathiazole derivatives in ≈60% total yield. After deacetylation, the tested major 1(S) epimers were found good competitive inhibitors of emulsin β-D-glucosidase whereas a 1 (R) counterpart had

  在回流的四氯化碳中用N-溴琥珀酰亚胺进行辐照处理后，得到2,3,4,6-四-O-乙酰基-1- S-（Z）-苯氢肟基-1-硫代-D-吡喃葡萄糖1和各种类似物，得到了新的约占总产率60％的螺环杂恶二唑衍生物。脱乙酰基后，发现被测试的主要1（S）差向异构体是乳化素β-D-葡萄糖苷酶的良好竞争性抑制剂，而1（R）对应异构体对该酶没有影响。
• Novel cyclization of D-glucopyranosyl-(Z)-thiohydroximates leading to new anomeric spiro oxathiazole derivatives
  作者：Jean-Pierre Praly、Sophie Boyé、Benoît Joseph、Patrick Rollin

  DOI：10.1016/s0040-4039(00)79171-4

  日期：1993.5

  Both α- and β- anomers of 2,3,4,6-tetra-O-acetyl-1-S-(Z)-benzhydroximoyl-1-thio-D-glucopyranose yielded, when treated with N-bromosuccinimide in refluxing carbon tetrachloride, the same mixture of new anomeric spiro oxathiazole derivatives in which the major epimer has a (S) configuration at the anomeric centre.

  当在回流碳中用N-溴代琥珀酰亚胺处理时，会生成2,3,4,6-四-O-乙酰基-1- S-（Z）-苯并氢肟基-1-硫代-D-吡喃葡萄糖的α-和β-端基异构体。四氯化物，与新的异头螺氧基恶二唑衍生物相同的混合物，其中主要差向异构体在异头中心具有（S）构型。
• Synthesis and anti-inflammatory activity of aromatic glucosinolates
  作者：Quan V. Vo、Craige Trenerry、Simone Rochfort、Jenny Wadeson、Carolina Leyton、Andrew B. Hughes

  DOI：10.1016/j.bmc.2013.07.049

  日期：2013.10

  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.