204396-77-0

Upstream product

• 14685-99-5 (-)-5-amino-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose 
• 103-72-0 phenyl isothiocyanate 

Relevant academic research and scientific papers

Nitrogen versus sulfur acylation in sugar thioureas: Regioselectivity and conformational consequences

The influence of steric and electronic effects in the regioselectivity of base-catalysed acetylation reactions of sugar thioureas and the structural and conformational properties of the resulting products have been investigated. Bulky alkyl substituents f

Synthesis and evaluation of calystegine B2 analogues as glycosidase inhibitors

A practical synthesis of polyhydroxylated 6-oxa-nor-tropanes incorporating the essential structural features of calystegine B2 from 5-deoxy-5-thioureido and 5-ureido-L-idofuranose precursors is presented. The methodology relies on the ability of pseudoamide-type nitrogen atoms (thiourea, urea, and carbamate) to undergo nucleophilic addition to the masked aldehyde group of the monosaccharide. The generated hemiaminal functionality may further undergo in situ intramolecular glycosidation to give the bicyclic aminoacetal compounds, the whole process being favored by the anomeric effect. A series of derivatives bearing different substituents at nitrogen has been prepared and screened against several glycosidases in comparison with xylonojirimycin-type piperidine analogues. Interestingly, strong and highly specific inhibition of bovine liver β-glucosidase was observed for 6-oxacalystegine B2 analogues incorporating aromatic pseudoaglyconic groups. On the basis of these data, a 1-azasugar inhibition mode is proposed for this family of glycomimetics.

Synthesis of calystegine B2 analogs by tandem tautomerization-intramolecular glycosylation of thioureidosugars

Ring-modified analogs of calystegine B2, a powerful glycosidase inhibitor of the polyhydroxy-nor-tropane series, have been prepared in one-pot reaction from thiourea-carbohydrate precursors via a tandem tautomerization-intramolecular glycosylat