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Synthesis of 2,3-O-(propane-1,2-diyl)- and 2,3-O-(3-hydroxypropane-1,2-diyl)-cyclomaltoheptaose |
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| Authors: | Jindrich Jindrich Kazuaki Harata Bengt Lindberg Josep Pitha Pia Seffers |
| Affiliation: | a Department of Organic Chemistry, Charles University, Alberthov 2030, 128 40, Praha 2, Czech Republic b Biomolecular Department, National Institute of Bioscience and Human-Technology, 1-1 Higashi, Tsukuba, Ibaraki 305, Japan c Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-10691, Stockholm, Sweden |
| Abstract: | 21,31-O-(Propane-1,2-diyl)cyclomaltoheptaose has been prepared from 2-O-allylcyclomaltoheptaose by mercuration in trifluoroacetic acid, followed by reduction with sodium borohydride. 2-O-(2,3-Epoxypropyl)cyclomaltoheptaose, prepared from 2-O-allylcyclomaltoheptaose by oxidation with dimethyldioxirane, was converted into 21,31-O-(3-hydroxypropane-1,2-diyl)cyclomaltoheptaose by treatment with trifluoroacetic acid. Both derivatives containing fused 1,4-dioxane rings are mixtures of stereoisomers, in which the methyl and hydroxymethyl group, respectively, that is linked to this ring, occupies an axial or an equatorial position. |
| Keywords: | Cyclodextrins 1,4-Dioxane rings fused to sugar residues |
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