同位素标记的1,3 - 二硫戊环的合成。
Synthesis of isotopically labeled 1,3-dithiane.
作者信息
Martinez Rodolfo A, Glass David R, Ortiz Erick G, Alvarez Marc A, Unkefer Clifford J
机构信息
Bioscience Division, Los Alamos National Laboratory, The National Stable Isotope Resource, MS E529, Los Alamos, NM, 87545, USA; Department of Chemistry, New Mexico Highlands University, Box 9000, Las Vegas, NM, 87701, USA.
出版信息
J Labelled Comp Radiopharm. 2014 May 15;57(5):338-41. doi: 10.1002/jlcr.3185. Epub 2014 Feb 7.
The 1,3-dithiane is a protected formaldehyde anion equivalent that could serve as a useful labeled synthon. We report a facile synthesis of 1,3-[2-(13)C]- and 1,3-[2-(13)C, 2-(2)H2]dithiane in two steps from [(13)C]- or [(13) C, (2)H3 ]methyl phenyl sulfoxide. We have previously reported the high yield synthesis of [(13)C]methyl phenyl sulfide from [(13)C]MEOH and the oxidation of [(13)C]methyl phenyl sulfide to [(13)C]methyl phenyl sulfoxide. Here, we describe the facile exchange of deuterium from (2) H2 O into [(13)C]methyl phenyl sulfoxide to yield [(13)C, (2)H3]methyl phenyl sulfoxide. Thus, from [(13)C]MEOH and (2)H2O, all possible C2 stable isotopomers of 1,3-dithiane are available. Our synthetic route is also amenable to preparation of radiolabeled 1,3-dithianes.
1,3 - 二硫戊环是一种受保护的相当于甲醛阴离子的物质，可作为一种有用的标记合成子。我们报道了一种从[(¹³)C] - 或[(¹³)C, (²)H₃]甲基苯基亚砜分两步轻松合成1,3 - [2 - (¹³)C] - 和1,3 - [2 - (¹³)C, 2 - (²)H₂]二硫戊环的方法。我们之前报道了由[(¹³)C]甲醇高产率合成[(¹³)C]甲基苯硫醚以及将[(¹³)C]甲基苯硫醚氧化为[(¹³)C]甲基苯基亚砜。在此，我们描述了将(²)H₂O中的氘轻松交换到[(¹³)C]甲基苯基亚砜中以生成[(¹³)C, (²)H₃]甲基苯基亚砜的过程。因此，从[(¹³)C]甲醇和(²)H₂O可以得到1,3 - 二硫戊环所有可能的C₂稳定同位素异构体。我们的合成路线也适用于制备放射性标记的1,3 - 二硫戊环。
Zotero 插件