Synthesis and biological evaluation of a small library of nojirimycin-derived bicyclic iminosugars

Expanding the Scope of Aminosugars: Synthesis of 2‐Amino Septanosyl Glycoconjugates Using Septanosyl Fluoride Donors

“…In the event, tri-O-benzyl xylose 10 is converted to the N-benzyl glycosyl amine 11 under known conditions. [13,15] Addition of a vinyl Grignard to the glycosyl amine (presumably in the hydroxy imine form) provided allylic amine 12 (50 % over two steps). Addition was highly stereoselective; we isolated only one diastereomer of 12, which was consistent with Grignard additions to glycosyl amines 4-6.…”

“…We argued that the protecting groups on the C2 amine were playing an important steric role for the selective formation of the cyclic acetal of a specific anomeric configuration. Anomeric stereochemistry was assigned by considering the Cram chelate model that sets C2 stereochemistry [15] in conjunction with 3 J H1,H2 coupling constants, the magnitudes of which (5.6-8.0 Hz) were diagnostic of a trans or anti configuration. Additionally, 13 C NMR chemical shifts of the C1 carbons were consistent with a and b assignments from other septanoses that have been prepared.…”

Synthesis of Novel Iminosugar‐Based Trehalase Inhibitors by Cross‐Metathesis Reactions

“…[15] Each monomer was homodimerized by CM using the 2nd generation Grubbs catalyst in dry dichloromethane as solvent.…”

Glycosidase inhibitors: versatile tools in glycobiology

“…It has been claimed that probably their intrinsic rigid structure is responsible for the biological activity exerted by many of these carbohydrate mimics. 61,62 Compounds like lentiginosine, swainsonine, and castanospermine (di, tri and tetrahydroxylated indolizidines), casuarine, and hyacinthacines (polyhydroxylated pyrrolizidines), and quinolizidines are remarkable examples. 1 A novel indolizidine alkaloid, (À)-steviamine 88, has recently been isolated from the leaf material of Stevia rebaudiana.…”