Adaptation of an NMR signal suppression pulse sequence for the selective removal of benzylic methylene signals of benzyl ether-protected carbohydrates

Tetrahedron Letters

Volumn 40, Issue 10, 1999, Pages 2025-2028

  Rutherford, Trevor J ^a   Kartha, K P Ravindranathan ^a   Readman, S Kristy ^a   Cura, Peter ^a   Field, Robert A ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; THIOGLYCOSIDE;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL REACTION; GLYCOSYLATION; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0033525837     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00108-2     Document Type: Article

References (11)

1. Iodine and its' interhalogen compounds: Useful reagents in carbohydrate chemistry X. For part IX see: Kartha, K.P.R.; Field, R.A. Synlett, in press. Further information about the NMR studies reported herein can be obtained from TJR at : School of Chemistry, The University of Birmingham, Edgbaston, Birmingham B15 2TT, e-mail: t.j.rutherford@bham.ac.uk
2. Hwang, T. L.; Shaka, A. J. J. Magn. Reson., Ser. A, 1995, 112, 275.
3. Xu, G.; Evans, J. S. J. Magn. Reson. B, 1996, 111, 183.
4. Gradwell, M. J.; Kogelberg, H.; Frenkiel, T. A. J. Magn. Reson., 1997, 124, 267.
5. Uhrín, D.; Barlow, P. N. J. Magn. Reson., 1997, 126, 248.
6. It should be noted that the peak integrals are dependent upon the efficiency of the spin-lock period, and are not an accurate measure of the relative concentration of separate signals. However, providing the pulse width calibration is unaffected by the changing sample conditions, any change of signal intensity is a quantitative measure of the change in concentration. The duration of a 90° pulse is a function of the magnetic susceptibility of the solvent, (which is affected by pH and ionic strength) but in this transformation the pulse width calibration before and after the experiment were identical.
7. Cura, P.; 1997, PhD thesis, University of St Andrews. Kartha, K.P.R.; Aloui, M.; Cura, P.; Readman, S.K.; Rutherford, T.J.; Field, R.A., manuscript in preparation.
8. 6
9. For the corresponding α-glucopyranosyl iodide see: Gervay, J.; Nguyen, T.N.; Hadd, M.J. Carbohydr. Res., 1997, 300, 119.
10. Boons, G.J.; Stauch, T. Synlett, 1996, 906.
11. Geen, H.; Freeman, R. J. Magn. Reson., 1993, 93, 93.