Convergent Synthesis of N,S-bis Glycosylquinolin-2-ones via a Pd-G3-XantPhos Precatalyst Catalysis.

ABSTRACT

Buchwald-Hartwig-Migita cross-coupling of 1-thiosugars with α- or ß-3-iodo-N-glycosylquinolin-2-ones has been accomplished under mild and operationally simple reaction conditions through the use of a Pd-G3 XantPhos palladacycle precatalyst. This new methodology has been successfully applied to a variety of α- or ß-mono-, di-, and poly-thiosugar derivatives to efficiently synthesize a series of α- or ß-N,S-bis-glycosyl quinolin-2-ones, which are difficult to synthesize by classical methods.