SYNTHESIS OF 2(1),3(1)-O-(PROPANE-1,2-DIYL)- AND 2(1),3(1)-O-(3-HYDROXYPROPANE-1,2-DIYL)CYCLOMALTOHEPTAOSE

摘要

2(1),3(1)-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 2(1),3(1)-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. (C) 1997 Elsevier Science Ltd. [References: 13]