silver imidazolate; zinc(II) chloride glycosylation;

boron trifluoride diethyl etherate; triethylamine in dichloromethane 120 h;

zinc(II) chloride

1: o-hydroxynitrobenzene With 1-n-butyl-3-methylimidazolium chloride; silver(l) oxide T=25°C; Koenigs-Knorr type coupling; 0.25 h; Darknessneat (no solvent); 2: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide T=25 - 80°C; Koenigs-Knorr type coupling; 0.5 h; Darknessneat (no solvent); optical yield given as percent destereoselective reaction;

1: acetic acid; HBr 2: acetone; potassium carbonate View Scheme

methanol; ammonia

1: Raney nickel; methanol / Hydrogenation 2: sodium methylate; methanol View Scheme