Accession Number : AD0674381

Title :   SYNTHESIS AND NUCLEAR MAGNETIC RESONANCE SPECTRA OF SOME PARTIALLY ACYLATED BETA-D-GLUCOPYRANOSIDES,

Corporate Author : NATIONAL RESEARCH COUNCIL OF CANADA SASKATOON (SASKATCHEWAN) PRAIRIE REGIONAL LAB

Personal Author(s) : Tulloch,A. P. ; Hill,A.

Report Date : 19 FEB 1968

Pagination or Media Count : 10

Abstract : The synthesis of ten new partially acylated derivatives of methyl beta-D-glucopyranoside, all with an acyl group at C-6, is described. The nuclear magnetic resonance spectra of these compounds, and of a number of related derivatives, have been measured using pyridine, acetone-d6, and deuteriochloroform as solvents. When OH-4 is acylated, the H-6 signals are at higher field (by 0.1-0.3 p.p.m.) than when OH-4 is not acylated, but this effect is not observed when OH-3 is acylated. When a trimethylsiyl ether group is introduced at C-4 the difference between the chemical shifts of the H-6 protons increases markedly. Estimation of J(BX) and J(AX) (where B is the H-6 proton at higher field and X is H-5), from spectra obtained using acetone-d6 and pyridine as solvents, shows that J(BX) < J(AX) when there is an acyl group at C-4 but J(BX) > J(AX) when there is no acyl group at C-4. (Author)

Descriptors :   (*GLYCOSIDES, MOLECULAR STRUCTURE), SYNTHESIS(CHEMISTRY), NUCLEAR MAGNETIC RESONANCE, MICROWAVE SPECTROSCOPY, STEREOCHEMISTRY, CANADA

Subject Categories : Biochemistry
      Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE