A selective and mild glycosylation method of natural phenolic alcohols

作者：Mastihubova Maria; Polakova Monika

来源：Beilstein Journal of Organic Chemistry, 2016, 12: 524-530.

DOI：10.3762/bjoc.12.51

<jats:p>Several bioactive natural <jats:italic>p</jats:italic>-hydroxyphenylalkyl β-D-glucopyranosides, such as vanillyl β-D-glucopyranoside, salidroside and isoconiferin, and their glycosyl analogues were prepared by a simple reaction sequence. The highly efficient synthetic approach was achieved by utilizing acetylated glycosyl bromides as well as aromatic moieties and mild glycosylation promoters. The aglycones, <jats:italic>p</jats:italic>-<jats:italic>O</jats:italic>-acetylated arylalkyl alcohols, were prepared by the reduction of the corresponding acetylated aldehydes or acids. Various stereoselective 1,2<jats:italic>-trans-O-</jats:italic>glycosylation methods were studied, including the DDQ–iodine or ZnO–ZnCl<jats:sub>2</jats:sub> catalyst combination. Among them, ZnO–iodine has been identified as a new glycosylation promoter and successfully applied to the stereoselective glycoside synthesis. The final products were obtained by conventional Zemplén deacetylation.</jats:p>

• 出版日期2016-3-15