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Boat Conformations: Synthesis, NMR Spectroscopy, and Molecular Modeling of Methyl 2,6-Anhydro-3-Deoxy-3-Phthalimido-Α-D-Mannopyranoside and its 15N-Labeled Analog

Published

Author(s)

B Coxon

Abstract

Methyl 2,6-anhydro-3-deoxy-3-phthalimido-α-D-mannopyranoside and its 15N-labeled analog have been synthesized by reaction of methyl 2,6:3,4-dianhydro-α-D-altropyranoside with a mixture of phthalimide and potassium phthalimide or their 15N-labeled analogs. The geometry of the twisted boat conformation of the mannopyranoside derivative has been characterized by molecular dynamics with simulated annealing and correlated with vicinal and long-range 1H-1H and vicinal 1H-15N coupling constants measured by 1H NMR spectroscopy. Dihedral angle comparisons have been made with derivatives of the parent 2,2,2-bicyclo-octane structure. The 1H-15N coupling constant data provide further values for definition of a Karplus equation for analysis of the stereochemistry of aminoglycosides.
Citation
Carbohydrate Research
Volume
322
Issue
No. 1-2

Keywords

13C-15N and 1H-15N coupling constants, 13C-1H chemical shift correlation, 2, 6-anhydro sugars, boat conformation, mannopyranoside, molecular dynamics, NMR spectroscopy, simulated annealing

Citation

Coxon, B. (1999), Boat Conformations: Synthesis, NMR Spectroscopy, and Molecular Modeling of Methyl 2,6-Anhydro-3-Deoxy-3-Phthalimido-&#913;-D-Mannopyranoside and its <sup>15</sup>N-Labeled Analog, Carbohydrate Research (Accessed May 19, 2024)

Issues

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Created November 1, 1999, Updated June 2, 2021