2-Deoxy-4-O-{2-deoxy-2-[(1-hydroxyethylidene)amino]hexopyranosyl}-2-[(1-hydroxyethylidene)amino]hexopyranose → HCID 131728351, compound

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Reaction Steps

To prepare trisaccharide oxazoline 3, the 4′,6′-O-benzylidene group in 15 was selectively removed by treatment with 80% aqueous AcOH at 50 C. The resulting compound 21 was then selectively glycosylated at the 6′-OH position with 2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl trichloroacetimidate under the catalysis of TMSOTf to give trisaccharide derivative 23 (76%). De-O-benzoylation of 23 with subsequent O-acetylation afforded the O-acetylated pentenyl glycoside 25. Finally, compound 25 was converted to the oxazoline derivative by treatment with NIS/TESOTf to give 26, which was de-O-acetylated to provide trisaccharide oxazoline 3. On the other hand, the known chitobiose oxazoline 6[15] and the LacNAc-oxazoline 7[16] were prepared from O-acetylated N,N′-diacetylchitobiose and N-acetyllactosamine, respectively, following the reported procedure.[15, 16]

Provenance & Evidence