(2S,3R,6S)-2-methyl-6-(phenylthio)-3,6-dihydro-2H-pyran-3-yl acetate | 125848-29-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2S,3R,6S)-2-methyl-6-(phenylthio)-3,6-dihydro-2H-pyran-3-yl acetate
• 英文别名: [(2S,3R,6S)-2-methyl-6-phenylsulfanyl-3,6-dihydro-2H-pyran-3-yl] acetate
• CAS: 125848-29-5
• 化学式: C₁₄H₁₆O₃S
• 分子量: 264.345
• InChiKey: DVEYUCCPQXQEML-GDLCADMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,6S)-2-methyl-6-(phenylthio)-3,6-dihydro-2H-pyran-3-yl acetate 在 哌啶 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 1,5-anhydro-4,6-di-O-acetyl-2-deoxy-D-xylo-hex-1-enitol
  参考文献：
  名称：

  A route to glycals in the allal and gulal series: synthesis of the thiosugar of esperamicin A1

  摘要：

  DOI：

  10.1021/jo00294a004
• 作为产物：
  描述：

  苯硫酚 、 3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以82 %的产率得到(2S,3R,6S)-2-methyl-6-(phenylthio)-3,6-dihydro-2H-pyran-3-yl acetate
  参考文献：
  名称：

  Tetrocarcin A 的四糖糖基部分的合成

  摘要：

  描述了 tetrocarcin A 的四糖片段的从头合成。这种方法的关键特征是区域选择性和非对映选择性 Pd 催化的烯-烷氧基丙二烯与未保护的l-洋地黄毒糖苷的加氢烷氧基化。随后与洋地黄醛的反应结合化学选择性氢化产生了目标分子。

  DOI：

  10.1021/acs.joc.2c02832

文献信息

• Pd-Catalyzed Umpolung Chemistry of Glycal Acetates and Their [2,3]-Dehydrosugar Isomers
  作者：Juyeol Lee、Young Ho Rhee

  DOI：10.1021/acs.orglett.1c04004

  日期：2022.1.21

  Glycals and their [2,3]-dehydrosugar derivatives have commonly been used in synthetic chemistry as electrophiles. Here we report a Pd-catalyzed polar inversion (umpolung) of this reaction, where the glycals and isomers can be used as nucleophiles. The reaction showed high regio- and stereoselectivity in the presence of numerous aromatic and aliphatic aldehydes. The synthetic utility of this reaction

  Glycals 和它们的 [2,3]-脱氢糖衍生物通常在合成化学中用作亲电子试剂。在这里，我们报告了该反应的 Pd 催化的极性反转（umpolung），其中糖基和异构体可用作亲核试剂。在大量芳香族和脂肪族醛的存在下，该反应显示出高区域选择性和立体选择性。该反应的合成效用通过抗癌天然产物粘液素的四氢吡喃片段的短合成得到证明。
• 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.
• WITTMAN, MARK D.;HALCOMB, RANDALL L.;DANISHEFSKY, SAMUEL J.;GOLIK, JERZY;+, J. ORG. CHEM., 55,(1990) N, C. 1979-1981
  作者：WITTMAN, MARK D.、HALCOMB, RANDALL L.、DANISHEFSKY, SAMUEL J.、GOLIK, JERZY、+

  DOI：——

  日期：——