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Synthesis of 3I-O and 2I-O-monosubstituted derivatives of per-6-azido-β-cyclodextrin-potential molecular scaffolds
M. Popr, S. Hybelbauerová, J. Jindřich,
Jazyk angličtina Země Nizozemsko
Typ dokumentu časopisecké články, práce podpořená grantem
Odkazy
PubMed
23023041
DOI
10.1016/j.carres.2012.09.003
Knihovny.cz E-zdroje
- MeSH
- azidy chemická syntéza chemie MeSH
- beta-cyklodextriny chemická syntéza chemie MeSH
- konformace sacharidů MeSH
- stereoizomerie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
Alkylation of per-6-azido-β-cyclodextrin by a suitable electrophilic reagent (cinnamyl bromide or propargyl bromide) gave a mixture of 3(I)-O and 2(I)-O regioisomers. After peracetylation and chromatographic separation on silica gel, pure isomers were isolated. Oxidative cleavage of cinnamyl double bond afforded the corresponding formylmethyl and carboxymethyl derivatives. The prepared scaffold molecules are equipped with two types of reactive groups which have a potential to serve as points of attachment for various compounds.
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