Stable analogues of nojirimycin – synthesis and biological evaluation of nojiristegine and manno-nojiristegine

Abstract

Two novel iminosugars called nojiristegines, being structural hybrids between nor-tropane alkaloid calystegine and nojirimycins, have been synthesised and found to be stable molecules despite the presence of a hemiaminal functionality. The synthesised iminosugars were evaluated against a panel of glycosidases and the best inhibition (IC50), found against α-glucosidases, was in the micromolar region. The compounds were also evaluated as potential antibiotics but no useful level of activity was observed.

Carbohydrate-Based Chiral Iodoarene Catalysts: A Survey through the Development of an Improved Catalyst Design

“…32 : Prepared from 29 (4.31 g, 6.10 mmol) accordingly to general procedure F; colorless syrup; 71% (2.00 g) yield after column chromatography (PE/EtOAc, 2/1 → 1/2); analytical data were in good accordance with literature values [31].…”

Vinyl Grignard-Mediated Stereoselective Carbocyclization of Lactone Acetals

“…Therefore, the anomeric epimer of 3 ( 12 ) and lactone acetals derived from d -mannose ( 16 ) and d ‑galactose ( 20 ) were synthesized (Scheme ). The syntheses resemble the synthesis of 3 , starting with conversion of the free alcohol into the iodide followed by elimination and ozonolysis. ,, …”

1,3-Dibromo-5,5-dimethylhydantoin as promoter for glycosylations using thioglycosides

“…Initially, the capability of DBDMH to activate thioglycoside 1 [ 32 ] in order to glycosylate the primary hydroxy group present in D-glucose acceptor 2 [ 33 ] was explored without any additives ( Table 1 , entry 1). This initial experiment furnished disaccharide 3 , albeit in modest yield (43%).…”