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Issue 23, 2018
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Macrocyclic derivatives with a sucrose scaffold: insertion of a long polyhydroxylated linker between the terminal 6,6′-positions

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Abstract

A series of five new macrocyclic hybrids with a sucrose scaffold were prepared by the reaction of activated 1′,2,3,3′,4,4′-hexa-O-methylsucrose with diversely functionalized D-mannitols. The 21-, 25-, and 31-membered representatives containing mannitol units were prepared by a macrocyclization of 6,6′-di-O-propargylated sucrose with protected 1,6-diazido-D-mannitol or 6,6′-di-azidosucrose with propargylated D-mannitol (a “click” approach), whereas 23-membered representatives were prepared by double N-alkylation of 1′,2,3,3′,4,4′-hexa-O-methyl-6,6′-di-aminosucrose with 1,6-di-bromoacyl D-mannitol. All sucrose derivatives were tested as putative hosts for chiral recognition of α-phenylethylammonium (α-PEA) cations. In one case, in striking contrast to all sucrose-based macrocyclic hosts previously reported by us, unexpected reverse preference for the R-enantiomer was observed (KR/KS = 1.5).

Graphical abstract: Macrocyclic derivatives with a sucrose scaffold: insertion of a long polyhydroxylated linker between the terminal 6,6′-positions

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Publication details

The article was received on 06 Jun 2018, accepted on 15 Oct 2018 and first published on 16 Oct 2018


Article type: Paper
DOI: 10.1039/C8NJ02808G
New J. Chem., 2018,42, 18578-18584

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    Macrocyclic derivatives with a sucrose scaffold: insertion of a long polyhydroxylated linker between the terminal 6,6′-positions

    B. Chaciak, K. Dąbrowa, P. Świder and S. Jarosz, New J. Chem., 2018, 42, 18578
    DOI: 10.1039/C8NJ02808G

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