Synthesis of 2-{2-[2-(N-Tert-Butyloxycarbonyl)Ethoxy]Ethoxy}Ethyl β-d-Glucopyranoside

Azidoalkyl glycosides are useful intermediates in the synthesis of their corresponding aminoalkyl glycoside counterparts, as well as in the preparation of glycoconjugates through azide-alkyne cycloadditions. Ethylene glycol-type linkers have other advantages over their aliphatic chain counterparts. They are known to be more water soluble and show lower immunogenicity and nonspecific binding character.9 Also, as pointed out, these spacer arms are considered to be superior to the poly(methylene) types, which have a strong tendency to coil in aqueous milieu, thus lessening their effective lengths. High-performance liquid chromatography (HPLC) grade solvents were used, and reactions requiring anhydrous conditions were carried out under nitrogen or argon. Hydrogenation/hydrogenolysis was done under atmospheric pressure.