Crystal Structure of Methyl 2,3-di-O-benzyl-α-d-(4-2H)-Glucopyranoside

Abstract Methyl 2,3-di- O -benzyl-α- d -(4- 2 H)-glucopyranoside, C 21 H 25 DO 6 , is an intermediate used in synthesis of oligosaccharides. The hexopyranose ring has the 4 C 1 chair conformation in the crystal structure. The exocyclic groups of the hexose sugar show for the glycosidic torsion angle ϕ =−52.8° and for the hydroxymethyl group the gauche - gauche conformation with ω = −64.7°, one of the two main orientations of the latter group in hexopyranose sugars that have the gluco -configuration, i.e., with an equatorial hydroxyl group at C4. The benzene rings of the benzyl groups are arranged with an angle of 56.9° to each other within the molecule and show intramolecular as well as intermolecular C-H ··· π interactions. A chain of intermolecular hydrogen bonds exists along the b-axis involving O4 and O6 atoms. The experimentally observed peak in the infrared spectrum at 2159 cm − 1 was ascribed to the stretching of the C4–D4 bond based on DFT calculations. Graphical Abstract