Crystal structure of 4-nitrophenyl 6-O-ethyl-β-D-galactopyranoside monohydrate

Abstract

The synthesis and crystal structure of the title compound, C14H19NO8·H2O, prepared in three steps from 6-O-ethyl-1,2;3,4-di-O-isopropylidene-α-D-galactopyranose using protecting-group strategies employed in carbohydrate chemistry, is reported. The asymmetric unit consists of a single galactoside molecule, in which the pyranoid ring has a4C1conformation and the 4-nitrophenyl moiety is essentially planar. In the crystal, each carbohydrate is surrounded by other D-galactose residues and water molecules, linked by O—H...O hydrogen bonds involving all hydroxy groups, giving a two-dimensional substructure lying parallel to (100) and extended into three dimensions by C—H...O interactions.