Preparation method of asymmetric disulfide compound

Abstract

The invention relates to a synthetic method of an asymmetric disulfide compound. According to the method, mercaptan which is convenient and easy to obtain and symmetrical disulfide compounds are usedas raw materials, and the asymmetric disulfide compounds are efficiently synthesized under the catalytic action of palladium salt or copper salt. The method has the advantages of accessible raw materials, simple catalytic system, high functional group compatibility, high yield and the like, and is convenient to operate. The method is particularly suitable for selectively introducing disulfide bonds into complex substrates, and can be widely applied to the industries of medicines, foods and the like.

Description

technical field [0001] The invention relates to a preparation method of an unsymmetrical disulfide compound. Background technique [0002] Due to the disulfide skeleton containing two covalently bonded sulfur atoms, disulfide compounds have unique pharmacological and physicochemical properties, and are important molecular structures in life sciences, pharmaceutical sciences, and food sciences. Disulfide bonds widely exist in many biologically active natural products and drug molecules, see Chinese Chemical Letters 2018, 29, 1079; Angew.Chem.Int.Ed.2018, 57, 12290. Plays a multifaceted role in various biochemical redox processes; the secondary and tertiary structures of proteins are also formed and stabilized by disulfide bridges, see Nat Commun, 2018, 9, 2191; Angew.Chem.Int.Ed .2015, 54, 9218; Tetrahedron Lett. 1990, 31, 2389. Therefore, disulfide compounds have important scientific significance and application value. Biological molecules containing disulfide bonds repor...

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Problems solved by technology

[0007] In 2006, Roy reported the synthesis of asymmetric disulfide compounds by sulfur compounds containing easily leaving groups (such as sulfur chloride compounds, LG=Cl) and mercaptans, but such raw materials are unstable and need to be prepared on the spot Use, the reaction operation is more complicated

[0009] In 2013, Parkin et al. reported the synthesis of asymmetric disulfides by starting from oxidized thiosulfoxides, but the raw material thiosulfoxides required selective oxidation of one of the sulfur atoms into sulfoxides, and there were peroxidation and two The sulfur atoms are all oxidized, so the synthesis process is more complicated

[0011] In 2018, Professor Lei Aiwen's research group reported the synthesis of asymmetric disulfides by electrochemical oxidation of S-H. Although this synthesis method is green and environmentally friendly, it is due to the oxidation potential of aromatic thiols and alkyl thiols. difference to achieve asymmetric synthesis of S-S bonds

[0015] In summary, most of the synthetic methods of asymmetric disulfide compounds have disadvantages such as long steps, cumbersome operation, many by-products, poor functional group compatibility, and limited substrates, which seriously restrict the development of asymmetric disulfide compounds. Applied Research of Compounds

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