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Abstract

Methyl 2,3-di-O-benzyl-alpha-d-(4-2H)-glucopyranoside, C21H25DO6, is an intermediate used in synthesis of oligosaccharides. The hexopyranose ring has the 4C1 chair conformation in the crystal structure. The exocyclic groups of the hexose sugar show for the glycosidic torsion angle phi =-52.8 degrees and for the hydroxymethyl group the gauche-gauche conformation with omega = -64.7 degrees, 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 degrees to each other within the molecule and show intramolecular as well as intermolecular C-Hpi 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 AbstractIn the structure of the monosaccharide methyl 2,3-di-O-benzyl-alpha-d-(4-2H)-glucopyranoside, C21H25DO6, the two hydroxyl groups HO4 and HO6 act as both donors and acceptors resulting in an intermolecular hydrogen bond chain along the b-axis direction.

Keywords

Crystal structure; Carbohydrate; Deuteration; Hydrogen bonding; Infrared

Published in

Journal of Chemical Crystallography
2025
Publisher: SPRINGER/PLENUM PUBLISHERS

SLU Authors

UKÄ Subject classification

Physical Chemistry
Inorganic Chemistry

Publication identifier

  • DOI: https://doi.org/10.1007/s10870-025-01051-8

Permanent link to this page (URI)

https://res.slu.se/id/publ/141939