The preparation and NMR analysis of 2,3-di-O-benzyl D-ribose and 2,3-di-O-D-xylose are described. In DMSO-d(6) the sugars adopt a conformation in which the hydroxyl groups are in an equatorial position. In CDCI3 and CD2Cl2 the sugars adopts a conformation in which intramolecular hydrogen bonding plays an important role in determining the equilibrium composition. These findings were also confirmed by DFT studies and, in the solid phase, by X-ray single crystal diffraction

Synthesis of 2,3-O-benzyl-ribose and xylose and their equilibration / Jeffrey, Reignier; Singh, Gurdial; Plaza Alexander, Patrice G. J.; Singh, Nadia; Goodman, Jonathan M.; Bacchi, Alessia; Punzo, Francesco. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 25:20-21(2014), pp. 1424-1429. [10.1016/j.tetasy.2014.09.004]

Synthesis of 2,3-O-benzyl-ribose and xylose and their equilibration

BACCHI, Alessia;
2014-01-01

Abstract

The preparation and NMR analysis of 2,3-di-O-benzyl D-ribose and 2,3-di-O-D-xylose are described. In DMSO-d(6) the sugars adopt a conformation in which the hydroxyl groups are in an equatorial position. In CDCI3 and CD2Cl2 the sugars adopts a conformation in which intramolecular hydrogen bonding plays an important role in determining the equilibrium composition. These findings were also confirmed by DFT studies and, in the solid phase, by X-ray single crystal diffraction
2014
Synthesis of 2,3-O-benzyl-ribose and xylose and their equilibration / Jeffrey, Reignier; Singh, Gurdial; Plaza Alexander, Patrice G. J.; Singh, Nadia; Goodman, Jonathan M.; Bacchi, Alessia; Punzo, Francesco. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 25:20-21(2014), pp. 1424-1429. [10.1016/j.tetasy.2014.09.004]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2787132
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