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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.
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 February 12, 2025)