Synthesis of (Z)-3-deoxy-3-(1,2,3,6-tetradeoxy-3,6-imino-L-arabino-hexitol-1-C-ylidene)-D-xylo-hexose derivatives. First examples of homo-(1-3)-C-linked imino-disaccharide

Cross-aldolisation of 3,6-[(/er/-butoxy)carbonyl]imino-2,3,6-trideoxy-4,5-0- isopropylidene-L-arafi/wo-hexose (10) with l,6-anhydro-2-0-benzyl-3-deoxy-P-Dery/ ftro-hexopyrano-4-ulose (6) generates, after water elimination, a single enone 11 that is reduced selectively into an allylic alcohol 12, deprotection of which affords methyl (Z)-3-deoxy-3-(l,2,3,6-tetradeoxy-3,6-imino-L-ara6/«o-hexitol-l-C-ylidene)-p-D-x>'/ohexofuranoside (1) and (2)-l,6-anhydro-3-deoxy-3-(l,2,3,6-tetradeoxy-3,6-imino-Lflra&/ HO-hexitol-l-C-ylidene)-P-D-;cy/o-hexopyranose(14).