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Syntheses and proton nmr and carbon 13 nmr spectra of all positional isomers of tetra o acetyl d glucopyranoses and their monobenzyl and monotrityl derivatives



Syntheses and proton nmr and carbon 13 nmr spectra of all positional isomers of tetra o acetyl d glucopyranoses and their monobenzyl and monotrityl derivatives



Chemical & Pharmaceutical Bulletin (Tokyo) 34(6): 2341-2353



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 (H- 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.

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