Syntheses and 1H- and 13C-Nuclear Magnetic Resonance Spectra of All Positional Isomers of Tetra-O-acetyl-D-glucopyranoses, and Their Monobenzyl and Monotrityl Derivatives

Abstract

All the isomers of the tetra-O-acetyl-D-glucopyranoses, and their monobenzyl and monotrityl derivatives were synthesized and systematic 1H- and 13C-nuclear magnetic resonance (1H- and 13C-NMR) studies were carried out. Complete assignments of the 1H- and 13C-NMR signals were achieved by 1H[1H]- and 13C[1H]-decoupling techniques and by the use of a shift reagent and changes of solvents. Moreover, when necessary, 1H[1H]- and 13C[1H]-shift-correlated 2D NMR spectroscopy at higher frequency (Bruker AM 400) was applied. The shifts on deacetylation, benzylation, and tritylation were estimated on the basis of the 1H- and 13C-chemical shifts of these compounds, and the effects of deacetylation and benzyl- or trityl-substitution are discussed. © 1986, The Pharmaceutical Society of Japan. All rights reserved.