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

Cross-aldolisation of 3,6-[(tert-butoxy)carbonyl]imino-2,3,6-trideoxy-4,5-O- isopropylidene-L-arabino-hexose (10) with 1,6-anhydro-2-O-benzyl-3-deoxy-beta-D-erythro-hexopyrano-4-ulose (6) generates, after water elimination, a single enone II that is reduced selectively into an allylic alcohol 12, deprotection of which affords methyl (Z)-3-deoxy-3-(1,2,3,6-tetradeoxy-3,6-imino-L-arabino-hexitol-1-C-yliden e)-beta-D-xylo-hexofuranoside (1) and (Z)-1,6-anhydro-3-deoxy-3-(1,2,3,6-tetradeoxy-3,6-imino-L-arabino-hexito l-1 -C-ylidene)-beta-D-xylo-hexopyranose (14).