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

Design and synthesis of a potential chitinase inhibitor 4, related to allos amidin (2), is described. Radical cyclization mediated by tributyltin hydri de was applied for the first time to chitobiose-derived oxime ethers 9a,b t o give four stereoisomers of an aminocyclopentane derivative connected to a n 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 cyc lic-guanidine formation reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.