Preparation of Sulfonyl Chlorides and Their Application in the Synthesis of Sulfonopeptides

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  Sulfonopeptides represent an important class of biologically active peptides,and have witnessed considerable applications in medicinal chemistry and clinical therapies.Sulfonopeptides have been synthesized mainly from 2-aminoalkanesulfonyl chlorides and amino esters or peptide esters.Recently,we developed three methods to prepare sulfonyl chlorides via the oxidative chlorination of the corresponding thiol precursors S-alkyl isothiourea salts or thiol derivatives with NCS-HCl,[1,2] NaClO2-HCl,[3] and NaClO-H2SO4.[4] The methods converted environment-and worker-friendly substrates into the corresponding sulfonyl chlorides in good to excellent yields.The desired sulfonopeptides were subsequently obtained in satisfactory to good yields by aminolysis of the synthesized sulfonyl chlorides with chiral α-amino esters.[5]
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