Autocatalytic condensation of 1,2-orthoesters of sugars with 2,3-dihydroxy-1,4-naphthoquinone (isonaphthazarin)
1989
The autocatalytic glycosylation of isonaphthazarine and its derivatives with 1,2-orthoesters of D-glucose and maltose in chlorobenzene has been studied. It has been established that the ratio of mono- and bisglycoside forms depends on the acidity of the glycosylated hydroxy group and its steric accessibility. Free monoglycosides of 2,3-dihydroxy-1,4-naphthoquinone have been synthesized by deacetylation with sodium methoxide in methanol.
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