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Boat Conformations Part IV- Synthesis, NMR Spectroscopy, and Molecular Dynamics of Methyl 4,6-O-Benzylidene-3-Deoxy-3-Phthalimido-alpha-D-Altropyranoside Derivatives

Published

Author(s)

B Coxon, R C. Reynolds

Abstract

dition of the elements of phthalimide to methyl 2,3-anhydro-4,6-O-benzylidene-α-D-mannopyranoside (1) under fusion conditions has yielded methyl 4,6-O-benzylidene-3-deoxy-3-phthalimido-α-D-altropyranoside(2). The conformation of the pyranose ring of 2 has been shown to be non-chair by 1H NMR spectroscopy, in contrast to the conformations of related derivatives having smaller substituents at C-3. Molecular dynamics simulations of 2 in explicit chloroform-d solvent have indicated four principal conformational possibilities. Of these, the 7C5/1S5 chair/skew boat form 2d has the lowest potential energy, and is largely consistent with the observed vicinal 1H--1H NMR coupling constants.
Citation
Carbohydrate Research
Volume
331
Issue
No. 4

Keywords

altropyranoside, boat conformations, H NMR Spectroscopy, molecular dynamics, phthalimidoderivative, simulated annealing, skew boat conformations, vicinal coupling constants

Citation

Coxon, B. and Reynolds, R. (2001), Boat Conformations Part IV- Synthesis, NMR Spectroscopy, and Molecular Dynamics of Methyl 4,6-O-Benzylidene-3-Deoxy-3-Phthalimido-alpha-D-Altropyranoside Derivatives, Carbohydrate Research (Accessed April 15, 2024)
Created April 1, 2001, Updated February 17, 2017