62858-36-0Relevant academic research and scientific papers
Halocyclization and palladium(II)-catalyzed amidocarbonylation of unsaturated aminopolyols. Synthesis of 1,4-iminoglycitols as potential glycosidase inhibitors
Huemmer, Walter,Dubois, Eric,Gracza, Tibor,Jaeger, Volker
, p. 634 - 642 (2007/10/03)
Syntheses of optically active 2,5-anhydro-1,4-dideoxy-1,4-iminoΔ- lyxitol (6), 1,4,5-trideoxy-1,4-imino-Δ-lyxo-hexitol (14), and its N-methyl derivative 15 from achiral divinylcarbinol, via the aminopentenediol 1, are described using halogen-promoted cyclization and Pd(II)-catalyzed amidocarbonylation as key steps. 2,5,6-Trideoxy-2,5-imino-Λ-ido-heptitol (23), a diastereomeric homologue of the naturally occurring pyrrolidine DMDP G, is prepared from Δ-glucosamine hydrochloride in 7 steps in 19% overall yield. The new compounds 6, 14,15, and 23 show weak glycosidase inhibition in two cases.
