R. Ferrier
1972
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Abstract
Publisher Summary This chapter discusses the applications of phenylboronic acid in carbohydrate chemistry. Phenylboronic acid condenses with diols to give cyclic esters that can be utilized in the synthesis of specifically substituted or oxidized sugar derivatives. In addition, it can be used in chromatographie solvents as a test reagent for cis -1,2,3-triols on pyranoid rings and, as its sulfonylated derivative, in electrophoretic separations of polyhydroxy compounds. In particular cases, it can be utilized in the isolation of compounds from mixtures. Though the majority are readily susceptible to hydrolysis and alcoholysis, phenylboronate esters are stable under esterifying, glycosylating, and certain oxidizing conditions, so that unprotected hydroxyl groups can be substituted or oxidized to keto functions. As the phenylboronate protecting group can be removed under mild, neutral conditions, these esters can be used for the synthesis of specific carbonyl derivatives or in the preparation of particularly substituted carbohydrate compounds.