Synthesis of a novel azapseudodisaccharide related to allosamidin employing N,N'-diacetylchitobiose as a key starting material

Article abstract of DOI:10.1016/S0040-4020(99)00972-2

Design and synthesis of a potential chitinase inhibitor 4, related to allosamidin (2), is described. Radical cyclization mediated by tributyltin hydride was applied for the first time to chitobiose-derived oxime ethers 9a,b to give four stereoisomers of an aminocyclopentane derivative connected to an N-acetyl-D- glucosamine residue at C-1 position. The major isomer 10b was efficiently converted into a novel pseudodisaccharide 4 via a series of cyclic-guanidine formation reaction.