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

November 1, 1999

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

Pub Type

Journals

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-Α-D-Mannopyranoside and its ¹⁵N-Labeled Analog, Carbohydrate Research (Accessed October 14, 2025)