Complete Sets of Monosubstituted γ-Cyclodextrins as Precursors for Further Synthesis

• DOI: 10.1021/jo301656p
• Publication Date: 2012-12-03T23:47:12Z
• Authors: Markéta Bláhová; Eva Bednářová; Michal Řezanka; Jindřich Jindřich
• Keywords: Allyl bromide; Propargyl; Propargyl bromide

Regioselective alkylation of γ-cyclodextrin with allyl or propargyl bromide, using optimized reaction conditions, followed by peracetylation the remaining hydroxyl groups and separation isomers resulted in set peracetylated 2I-O-, 3I-O- 6I-O-alkylated cyclodextrins up to 19% yields. Ozonolysis oxidative cleavage derivatives a complete 3I-O-, 6I-O-formylmethyl -carboxymethyl derivatives. All these are useful precursors for further preparation regioselectively monosubstituted γ-cyclodextrin.