A new class of amino protecting group removable by reductive acidolysis: the 4-methylsulphinylbenzyloxycarbonyl (Msz) group

Abstract

A safety-catch type of amino protecting group, the 4-methylsulphinylbenzyloxycarbonyl (Msz) group is stable under both acidic and basic conditions, but can be smoothly removed by a one-pot reaction involving reductive acidolysis using tetrachlorosilane–trifluoroacetic acid–scavengers; this new N-Msz group was successfully applied to the synthesis of a tachykinin peptide, scyliorhinin I, by a new orthogonal protection methodology.