Stereo- and Regioselective Synthesis of O-Mannosyl Glycan Containing Matriglycan and a Part of Tandem Ribitol Phosphate.

We herein successfully synthesized two pivotal structures of O-mannosyl glycan: (1) the matriglycan-repeating tetrasaccharide Xylα1-3GlcAβ1-3Xylα1-3GlcAβ and (2) the link between matriglycan and a part of tandem ribitol phosphate, Xylα1-3GlcAβ1-4Xylβ1-4Rbo, in a regio- and stereocontrolled manner. The disaccharide unit with the α-linkage of xylose was obtained by adopting the conformational fixation of the xylopyranoside ring and a specific solvation system of diastereoselective solubility.