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

Natural product family 18 chitinase inhibitors

“…6). Siriwardena et al 65 have provided a comprehensive discussion of the various derivatives synthesised up to 1999, while more recent contributions are to be found in the work of Takahashi et al, 95 Peter et al…”

Stereoselective Access to the β‐D‐N‐Acetylhexosaminyl‐(1→4)‐1‐deoxy‐D‐nojirimycin Disaccharide Series Avoiding the Glycosylation Reaction

“…Similar approaches have also been used by Stutz et al to prepare new iminosugar disaccharides starting from cellobiose,12 maltose12 and maltulose 13. Sporadic examples of hexosaminyl‐containing iminosugar disaccharides have been reported, and these compounds have been investigated as potential heparanase inhibitors,14 aza‐analogues of the repeating unit in peptidoglycan,15 potential endoglycosidase inhibitors,16 azapseudodisaccharides related to allosamidin,17 and transition‐state analogues for lysozyme 18. Owing to the interest in this rather unexplored class of azadisaccharides, we turned our attention to the synthesis of four representatives 1 – 4 (Figure 2), applying the double reductive amination strategy developed in our previous work 11…”

Synthesis, antiasthmatic, and insecticidal/antifungal activities of allosamidins

“…It is a new family-18 chitinase inhibitor, named allosemidin 1 . The compound has a unique chemical structure and its synthetic method is very challenging 3–29 . The selection of glycosylation methods to assemble the structural units of allosamidin and its analogues is the essential difference between each reported total synthesis method.…”