A concise synthesis of four C-3 fluoro/chloro-D-xylono-δ-lactams 3/4 has been reported. The methodology involves Corey-Link approach with suitably protected 3-oxo-D-gluco-furanose to introduce F/Cl as well as ester/amide functionalities at C-3 of glucose. In next steps, 5,6-O-isopropylidene group was converted to the 5-azido xylosugars that on opening of 1,2-acetonide group, and intramolecular Schmidt-Boyer reaction with TFA/H2O, in one pot, afforded lactams 3/4. Conformational aspect of δ-lactams was studied by the 1H NMR spectroscopy. The halogenated δ-lactams 3/4 showed no inhibition against different glycosidase enzymes.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/j.carres.2014.10.023 | DOI Listing |
Publication Analysis
Top Keywords
halogenated d-xylono-δ-lactams
4
d-xylono-δ-lactams synthesis
4
synthesis enzyme
4
enzyme inhibition
4
inhibition study
4
study concise
4
concise synthesis
4
synthesis c-3
4
c-3 fluoro/chloro-d-xylono-δ-lactams
4
fluoro/chloro-d-xylono-δ-lactams 3/4
4
Similar Publications
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!