Silicon‐29 and carbon‐13 n.m.r. studies of organosilicon chemistry. VIII—Assignment of the 29Si and related 1H resonances of trimethylsilylated sugars by deuteration and shift reagent studies
- 1 July 1977
- journal article
- Published by Wiley in Magnetic Resonance in Chemistry
- Vol. 9 (7) , 432-437
- https://doi.org/10.1002/mrc.1270090713
Abstract
Two techniques were investigated for assigning the 29Si n.m.r. spectra of trimethylsilylated sugars. Specific deuteration, together with selective proton decoupling experiments, has allowed the complete assignment for methyl 2,3,4,6‐tetra‐O‐trimethylsilyl‐α‐D‐glucopyranoside. Double resonance spectra obtained in the presence of a lanthanide shift reagent, Pr(dpm)3, have enabled the 29Si and 1H signals for the ‐SiMe3, groups of methyl 2,3,4‐tri‐O‐trimethylsilyl‐α‐D‐glucopyranoside, to be linked. A complete and unambiguous assignment of the 29Si spectrum for this molecule was obtained by selective deuteration, thus giving an unequivocal assignment of the –SiMe3 proton resonances also. Definitive data regarding the effects of Pr(dpm)3 on the 29Si and 1H resonances of the various –SiMe3 groups of methyl 2,3,4‐tri‐O‐trimethylsilyl‐α‐D‐glucopyranoside are therefore available.Keywords
This publication has 16 references indexed in Scilit:
- Application of 29Si-NMR to analysis of silylated compounds. NMR spectra of (CH3)3Si-O-C derivativesCollection of Czechoslovak Chemical Communications, 1976
- 29Si and 13C NMR studies of organosilicon chemistry. V—Sugar derivativesMagnetic Resonance in Chemistry, 1975
- Paramagnetic lanthanide shift reagents in NMR spectroscopy: Principles, methodology and applicationsProgress in Nuclear Magnetic Resonance Spectroscopy, 1973
- Lanthanide shift reagents for nuclear magnetic resonance spectroscopyChemical Reviews, 1973
- Solvent effects on the isotropic shifts and magnetic susceptibility of the shift reagent tris(dipivaloylmethanato)europium(III)Inorganic Chemistry, 1972
- Utility of Shift Reagents in Nuclear Magnetic Resonance Studies of Polyfunctional Compounds: N- and O-Acetylated Carbohydrates and NucleosidesCanadian Journal of Chemistry, 1971
- Spectres de RMN de quelques derives de sucres en presence de chelates de terres raresTetrahedron, 1971
- Synthesis and 13C N.M.R. spectrum of D-glucose-3-d. bond-polarization differences between the anomers of D-glucoseCarbohydrate Research, 1970
- Paramagnetic shifts in solutions of cholesterol and the dipyridine adduct of trisdipivalomethanatoeuropium(III). A shift reagentJournal of the American Chemical Society, 1969
- The Nuclear Magnetic Resonance of Some Paramagnetic Transition Metal AcetylacetonatesJournal of the American Chemical Society, 1965