2-Acetamido-N-benzyl-1,4-imino-1,2,4-trideoxy-L-ribitol

Abstract

The relative configuration of the stereocentres in a potential hexosaminidase inhibitor, C14H20N2O3, prepared from d‐lyxonolactone, has been established using X‐ray crystallographic techniques.

2-Acetamido-N-benzyl-1,4-imino-1,2,4-trideoxy-L-arabinitol 0.33-hydrate

“…A systematic study of the stereoisomers of a set of pyrrolidine analogues, (3), as potential NAG inhibitors (Harding et al, 2005) is in progress. Both enantiomers of imino sugars are frequently inhibitors of the same enantiospecific enzyme Asano et al, 2005;Yu et al, 2004).…”

Enantiomeric 2-acetamido-1,4-dideoxy-1,4-iminoribitols as potential pyrrolidine hexosaminidase inhibitors

“…Reaction of the aminodiol 21L with acetic anhydride in pyridine afforded the triacetyl derivative 22L (85% yield). The O-acetyl groups in 22L were selectively removed by treatment with catalytic sodium methoxide in methanol to give N-benzyl-LRBNAc 13L, in 91% yield; the structure of 13L was unequivocally established by X-ray crystallographic analysis [31]. Removal of the N-benzyl group in 13L by hydrogenolysis in the presence of palladium black in aqueous 1,4-dioxane gave LRBNAc 12L in 88% yield.…”