| 1412896-20-8

• 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
• CAS: 1412896-20-8
• 化学式: C₁₄H₂₀O₇S
• 分子量: 332.375
• InChiKey: MRSZSVNUEKTSPD-OUCADQQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  3-巯基丙酸甲酯 、 乙酰化葡萄烯糖 在 锆 作用下， 以 乙腈 为溶剂， 以50%的产率得到
  参考文献：
  名称：

  org/10.1016/j.tetlet.2012.09.023

  摘要：

  DOI：

  org/10.1016/j.tetlet.2012.09.023

文献信息

• Ferrier rearrangement promoted by an electrochemically generated zirconium catalyst
  作者：Dragana Stevanović、Anka Pejović、Ivan Damljanović、Aleksandra Minić、Goran A. Bogdanović、Mirjana Vukićević、Niko S. Radulović、Rastko D. Vukićević

  DOI：10.1016/j.carres.2015.02.001

  日期：2015.4

  In situ generated zirconium catalyst from a sacrificial zirconium anode was successfully applied to promote Ferrier rearrangement of 3,4,5-tri-O-acetyl-D-glucal and 6-deoxy-3,4-di-O-acetyl-L-glucal (3,4-di- O-acetyl-L-rhamnal) in the presence of three thiols and eleven thiophenols as nucleophiles. A simple constant current electrolysis (20 mA, 0.4 F mol(-1)) of an acetonitrile solution of lithium perchlorate (0.1 M) containing the corresponding glycal and S-nucleophiles, using a zirconium anode and a platinum cathode resulted in the successful synthesis of the corresponding 2,3-unsaturated peracetylated thioglycosides (with an average anomer ratio alpha/beta-4.129 in the case of peracetylated D-glucal and 8.740 in the case of L-rhamnal). The same procedure proved to be appropriate in synthesizing dihydropyran derivatives ('C-glycosides') using allyltrimethylsilane as the nucleophile (only 'alpha-anomers' were obtained). All new compounds were fully characterized by spectral data, whereas single-crystal X-ray analysis was performed for two thioglycosides. (C) 2015 Elsevier Ltd. All rights reserved.