Complete sets of monosubstituted γ-cyclodextrins as precursors for further synthesis
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
23205761
DOI
10.1021/jo301656p
Knihovny.cz E-resources
- MeSH
- Alkylation MeSH
- gamma-Cyclodextrins chemical synthesis chemistry MeSH
- Magnetic Resonance Spectroscopy MeSH
- Molecular Structure MeSH
- Oxidation-Reduction MeSH
- Pargyline analogs & derivatives chemistry MeSH
- Stereoisomerism MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- gamma-Cyclodextrins MeSH
- Pargyline MeSH
- propargyl bromide MeSH Browser
Regioselective alkylation of γ-cyclodextrin with allyl or propargyl bromide, using optimized reaction conditions, followed by peracetylation of the remaining hydroxyl groups and separation of isomers resulted in the set of peracetylated 2(I)-O-, 3(I)-O- and 6(I)-O-alkylated cyclodextrins in up to 19% yields. Ozonolysis or oxidative cleavage of peracetylated allyl derivatives resulted in a complete set of peracetylated 2(I)-O-, 3(I)-O-, and 6(I)-O-formylmethyl or -carboxymethyl derivatives. All of these derivatives are useful precursors for further preparation of regioselectively monosubstituted derivatives of γ-cyclodextrin.
References provided by Crossref.org
Mono-6-Substituted Cyclodextrins-Synthesis and Applications
Cyclodextrin-Polypyrrole Coatings of Scaffolds for Tissue Engineering
