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A convenient synthesis of a permethyl‐substituted β‐cyclodextrin‐containing polysiloxane stationary phase using an amide linking group
Author(s) -
Yi Guoliang,
Li Wenbao,
Bradshaw Jerald S.,
Malik Abdul,
Lee Milton L.
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320608
Subject(s) - chemistry , amide , cyclodextrin , group (periodic table) , phase (matter) , stereochemistry , organic chemistry , medicinal chemistry , polymer chemistry
A novel amide‐linked permethyl‐substituted β‐cyclodextrin‐bound polysiloxane stationary phase was prepared in only four steps. First, mono(6‐ O ‐toluenesulfonyl)‐β‐cyclodextrin was treated with sodium azide. Second, the resulting azide derivative was treated with methyl iodide and base followed by reduction with hydrogen to give amine‐substituted permethylcyclodextrin 3 . Third, cyclodextrin 3 was treated with p ‐(allyloxy)benzoyl chloride to form 6 A ‐( p ‐allyloxybenzamido)‐substituted permethyl‐β‐cyclodextrin 4 . Lastly, β‐cyclodextrin 4 was hydrosilylated onto a polysiloxane backbone containing hydrogen, methyl, and p ‐tolyl substituents. This new phase separated the enantiomers of certain chiral lactones and alcohols in capillary supercritical fluid chromatography.