404354-07-0Relevant academic research and scientific papers
Syntheses of imido-substituted glycosans and their photocyclisation towards highly functionalised heterotricycles
Thiering, Swantje,Sund, Christian,Thiem, Joachim,Giesler, Anja,Kopf, Juergen
, p. 271 - 282 (2001)
Reaction of O-protected amino-1,6-anhydro-β-D-hexopyranoses with succinic or glutaric anhydride and subsequent intramolecular acylation afforded the succinimido- and glutarimido-substituted glycosans. Irradiation with UV light of 254 nm wavelength led to γ-hydrogen abstraction at the pyranose ring by the excited carbonyl function. The stereoselective recombination of the resulting 1,4-diradicals gave annelated azetidinols, which fragmented by a retrotransannular ring opening reaction to give the glycosan-annelated azepanedione and azocanedione systems, respectively.
