129592-62-7

Upstream product

• 123533-16-4 (2R,3S)-1-amino-pent-4-ene-2,3-diol 
• 129570-41-8 (2R,3S)-N-(2,3-dihydroxypent-4-enyl)-4-methylbenzenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 129570-45-2 (1S,4S,7R)-7-Hydroxy-2-oxa-5-aza-bicyclo[2.2.1]heptane-5-carboxylic acid benzyl ester 
• 129570-43-0 2,5-anhydro-1,4-dideoxy-1,4-imino-N-tosyl-D-lyxitol 
• 129570-43-0 (1S,4S,7R)-5-(Toluene-4-sulfonyl)-2-oxa-5-aza-bicyclo[2.2.1]heptan-7-ol 

Relevant academic research and scientific papers

Halocyclization and palladium(II)-catalyzed amidocarbonylation of unsaturated aminopolyols. Synthesis of 1,4-iminoglycitols as potential glycosidase inhibitors

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.