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Halogen Azide Displacement to Prepare Some Symmetrically Substituted β‐Cyclodextrin Derivatives
Author(s) -
Szurmai Zoltán,
Lipták András,
Szejtli József
Publication year - 1990
Publication title -
starch ‐ stärke
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.62
H-Index - 82
eISSN - 1521-379X
pISSN - 0038-9056
DOI - 10.1002/star.19900421109
Subject(s) - yield (engineering) , cyclodextrin , halogen , azide , chemistry , methyl iodide , nuclear magnetic resonance spectroscopy , medicinal chemistry , iodide , combinatorial chemistry , stereochemistry , organic chemistry , materials science , alkyl , metallurgy
The heptakis (2,3‐di‐O‐acetyl‐6‐bromo‐6‐deoxy)‐β‐cyclodextrin has been converted to the 6‐azido derivate with 82% yield, then deacetylated by the Zemplén 's method (yield 75%) and methylated by methyl‐iodide (yield 66%), to heptakis (2,3‐di‐O‐methyl‐6‐azido‐6‐deoxy)‐β‐cyclodextrin, which is an appropriate intermediary toward methylated amino‐CD‐derivatives. The structure of all compounds were unambiguously proven by NMR spectroscopy.