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<p>Methyl 2,3-di-<i>O</i>-benzyl-α-<span>d</span>-(4-<sup>2</sup>H)-glucopyranoside, C<sub>21</sub>H<sub>25</sub>DO<sub>6</sub>, is an intermediate used in synthesis of oligosaccharides. The hexopyranose ring has the <sup>4</sup><i>C</i><sub>1</sub> chair conformation in the crystal structure. The exocyclic groups of the hexose sugar show for the glycosidic torsion angle <i>ϕ</i> =−52.8° and for the hydroxymethyl group the <i>gauche</i>-<i>gauche</i> conformation with <i>ω</i> = −64.7°, one of the two main orientations of the latter group in hexopyranose sugars that have the <i>gluco</i>-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<b>···</b>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&#xa0;cm<sup>− 1</sup> was ascribed to the stretching of the C4–D4 bond based on DFT calculations.</p> Graphical Abstract <p></p>

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

  • 期刊论文

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  • 发表日期：

    2025年5月14日

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  • Hani Mobarak,
  • Vadim Kessler,
  • Lars Eriksson,
  • Göran Widmalm

摘要

Methyl 2,3-di-O-benzyl-α-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 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