chapter  13
6 Pages

Squaric Acid Diethyl Ester–Mediated Homodimerization of Unprotected Carbohydrates

Experimental Methods ........................................................................................... 108 General Methods ............................................................................................... 108

p-{N-[4-(4-Aminophenyl α-d-glucopyranosyl)-2,3-dioxocyclobut-1enyl]amino}phenyl α-d-glucopyranoside (3a) ............................................. 108 p-{N-[4-(4-Aminophenyl β-d-glucopyranosyl)-2,3-dioxocyclobut-1enyl]amino}phenyl β-d-Glucopyranoside (3b) ............................................ 109

Acknowledgments .................................................................................................. 109 References .............................................................................................................. 112

of Tietze4 proteins.1 Moreover, the combination of glycosides bearing an amine (2 equivalents or more) with squaric acid ester (1 equivalent) leads to divalent glycosides, which are valuable medically relevant synthetic tools.5 Linker rigidity between two carbohydrates can modulate the cross-linking ability of various lectins.6 It is thus important to construct efciently a variety of rigid linkers to study the interactions between lectins and divalent sugar ligands.