An NMR approach for the determination of the substitution pattern in mono-modified cyclodextrins

Tetrahedron Letters

Volumn 40, Issue 49, 1999, Pages 8533-8537

  Forgo, Peter ^a   D'Souza, Valerian T ^a  

^a UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

Cyclodextrins; HSQC; Modified cyclodextrins; NMR; Selective long range INEPT

Indexed keywords

CYCLODEXTRIN; PROTON;

ARTICLE; ISOMERISM; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 0033520973     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01822-5     Document Type: Article

References (28)

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22. HMBC signals have dispersive components which hinder the extraction of projections from this spectrum. HMBC row at the substituted carbon has many correlations to protons in the same glucose unit which makes the assignment difficult.
23. The HSQC spectrum provides absorptive signals which facilitate extraction of a projection at the substituted carbon which has only one signal in the row.
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26. Accurate assignment of regiochemistry have been made in the past (Refs. 8 and 13) based on these chemical shift differences in conjunction with information available from the synthetic methodology.
27. The sevenfold symmetry of the ß-cyclodextrin is broken by the selective substitution in all three cases resulting in a crowded approximately 0.7 ppm wide chemical shift region around 3.8 ppm (bottom row in Fig. 2).
28. The anomeric proton H-l is equatorial because of the α-conformation of the sugar ring.