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An improved synthesis of 6-deoxy-analogues of cyclodextrins and amylose: Further interpretations of the proton magnetic resonance spectra of the peracetates of cyclodextrins and amylose



An improved synthesis of 6-deoxy-analogues of cyclodextrins and amylose: Further interpretations of the proton magnetic resonance spectra of the peracetates of cyclodextrins and amylose



Starke 26 (4) 111-118



A convenient procedure for the synthesis of 6-deoxy-analogues of cyclodextrins and amylose was developed. Selective bromination of primary hydroxyl groups in these compounds, and subsequent reductive debromination of the 2,3-di-O-acetates lead to the corresponding 6-deoxy-derivatives after deacetylation. The conformation of the 2,3-di-O-acetates of 6-bromo-6-deoxy- and 6-deoxy-analogues of the dextrins and amylose was investigated by PMR-spectroscopy. Furthermore, the chemical shift changes due to the modification at the C-6 position was studied for the ring and acetyl-methyl protons.

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Accession: 015022527

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DOI: 10.1002/star.19740260403


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