| 1412896-24-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• CAS: 1412896-24-2
• 化学式: C₁₄H₂₂O₅S
• 分子量: 302.392
• InChiKey: WHJKTFISLXWPKU-MJBXVCDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  丁硫醇 、 乙酰化葡萄烯糖 在 lithium perchlorate 作用下， 以 乙腈 为溶剂， 反应 0.53h， 以4%的产率得到
  参考文献：
  名称：

  Ferrier rearrangement promoted by an electrochemically generated zirconium catalyst

  摘要：

  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.

  DOI：

  10.1016/j.carres.2015.02.001

文献信息

• org/10.1016/j.tetlet.2012.09.023
  作者：Stevanovic, Dragana、Pejovic, Anka、Damljanovic, Ivan、Vukic evic, Rastko D.、VukiC evic, Mirjana、Bogdanovic, Goran A.

  DOI：org/10.1016/j.tetlet.2012.09.023

  日期：——
• Ruthenium Catalyzed Stereo/Chemo/Regioselective One-Pot Synthesis of C(2)–C(3) Unsaturated and α-<scp>d</scp>-Mannopyranosyl Sulfones
  作者：Sravanthi Chittela、Thurpu Raghavender Reddy、Palakodety Radha Krishna、Sudhir Kashyap

  DOI：10.1021/acs.joc.5b00975

  日期：2015.7.17

  An efficient and divergent approach to C(2)-C(3) unsaturated glycosyl and a-p-mannopyranosyl sulfones has been developed via ruthenium-promoted direct glycosylation, oxidation, and dihydroxylation from glycal in one-pot. The presence of stoichiometric amounts of NaIO4 and in situ generation of RuO4 from a RuCl3-NaIO4 reagent system were crucial for chemoselective oxidation of sulfide in the presence of an olefin moiety. The dual-role of ruthenium in sequential glycosylation-oxidation-dihydroxylation is amenable to a wide range of thio acceptors to access alpha-n-mannopyranosyl sulfones in good yields with high regioselectivity.