A straightforward route to a C-galactopyranosyl-linked 1,2-ethylenediamine is described. The five-step synthetic procedure involves: (i) C-allenylation of D-galactopyranose pentaacetate with propargyl trimethylsilane in the presence of a Lewis acid, (ii) iodination of allenyl galactopyranosyl tetraacetate to diiodoallyl galactopyranosyl tetraacetate, (iii) displacement of the allylic iodide with N-Boc-ethylenediamine, (iv) catalytic hydrogenation of vinyl iodide to alkane, (v) deprotection of the acetyl and N-Bocgroups using acid-catalyzed hydrolysis. This method demonstrates a general method to access a new class of carbohydrate?ethylenediamine C-glycosyl chelators.
Authors : Uthai Sakee,Chiradet Nasuk
Book /Journal Title : Carbohydrate Research ;2010 / 345 / 1222-1224