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Issue 12, 1976
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Assignment of 13C and 1H resonances of methyl groups in the tri-O-methyl derivatives of methyl pentopyranosides; some observations on the methoxy 13C chemical shifts

Abstract

By studies of specifically labelled trimethyl ethers of methyl β-L-arabinopyranoside, methyl α-D-lyxopyranoside, methyl β-D-ribopyranoside, and methyl α-D-xylopyranoside, in which some methyl groups are replaced by trideuteriomethyl groups, the 13C and 1H resonances of each of the methyl groups were identified. A rationalization is presented, in terms of syn-axial δ-effects and rotamer populations, for the deshielding experienced in six-membered rings by carbon-13 nuclei in equatorially disposed methoxy-groups, which are flanked by two equatorially attached methoxy(hydroxy)-groups. Benzoylation of methyl β-L-arabinopyranoside with benzoyl cyanide was shown, by 13C n.m.r. spectroscopy, to afford the 2,4-dibenzoate as the major product.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1976, 1351-1357
Article type
Paper

Assignment of 13C and 1H resonances of methyl groups in the tri-O-methyl derivatives of methyl pentopyranosides; some observations on the methoxy 13C chemical shifts

S. A. Abbas, A. H. Haines and A. G. Wells, J. Chem. Soc., Perkin Trans. 1, 1976, 1351
DOI: 10.1039/P19760001351

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