687992-26-3Relevant academic research and scientific papers
The intramolecular conjugate addition of benzylamine to a D-glucose derived α,β-unsaturated ester: An efficient synthesis of trihydroxylated pyrrolidine alkaloids as potential glycosidase inhibitors
Chaudhari, Vinod D.,Kumar, K.S. Ajish,Dhavale, Dilip D.
, p. 8363 - 8366 (2007/10/03)
A short and efficient synthesis of 1,4,5-trideoxy-1,4-imino-l-xylo-hexitol 2a and 1,4,5-trideoxy-1,4-imino-d-arabino-hexitol 2b is reported using the intramolecular conjugate addition of in situ generated benzylamine to the α,β-unsaturated ester 4, derived from d-glucose, as the key step.
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.
