Synthesis of 3-aminopropyl glycosides of linear β-(1→3)-d-glucooligosaccharides

Article abstract of DOI:10.1016/j.carres.2015.10.012

3-Aminopropyl glycosides of a series of linear β-(1→3)-linked d-glucooligosaccharides containing from 3 to 13 monosaccharide units were efficiently prepared. The synthetic scheme featured highly regioselective glycosylation of 4,6-O-benzylidene-protected 2,3-diol glycosyl acceptors with a disaccharide thioglycoside donor bearing chloroacetyl groups at O-2′ and -3′ as a temporary protection of the diol system. Iteration of the deprotection and glycosylation steps afforded the series of the title oligoglucosides differing in length by two monosaccharide units. A novel procedure for selective removal of acetyl groups in the presence of benzoyl ones consisting in a brief treatment with a large excess of hydrazine hydrate has been proposed.