New access to 1-deoxynojirimycin derivatives via azide-alkene cycloaddition.
The synthesis of 1-deoxynojirimycin (DNJ) derivatives is described from D-glucono-delta-lactone. The DNJ derivatives were obtained via a sequence that included a stereoselective intramolecular Huisgen reaction, decomposition to an aziridine, and its subsequent reaction with a nucleophile. Minimization of allylic strain in the transition state accounts for the stereoselectivity of the cycloaddition reaction.
Zhou
Ying
Y
UCD School of Chemistry and Chemical Biology and Centre for Synthesis and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland.
Murphy
Paul V
PV
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D005942:Gluconates / Q000737:chemistry*; D007783:Lactones; D013237:Stereoisomerism
D004791:Enzyme Inhibitors; D005942:Gluconates; D007783:Lactones; D017485:1-Deoxynojirimycin; C010730:beta-glucono-1,5-lactone