Synthesis of the Mycobacterium tuberculosis Canetti Lipooligosaccharide II Nonasaccharide

A route for preparing lipooligosaccharide (LOS) glycans from Mycobacterium tuberculosis Canetti was developed and applied to the most complex of these structures, LOS II. The synthesis of the target nonasaccharide was achieved via a convergent [3+3+3] approach. Key features of the strategy include the stereoselective synthesis of an asymmetrically substituted trehalose moiety from two protected glucose residues and several chemoselective glycosylations involving thioglycoside donors.