期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 12, 期 -, 页码 524-530出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.12.51
关键词
diastereoselectivity; p-hydroxyphenylalkyl glycosides; mild promoters; natural products; 1,2-trans-glycosylation
资金
- Slovak Research and Development Agency [APVV-846-12]
- Scientific Grant Agency of the Ministry of Education of Slovak Republic
- ERDF (Centre of Excellence on Green Chemistry Methods and Processes, CEGreenI) [26240120001]
- Slovak Academy of Sciences (VEGA) [2/0138/12]
- ERDF (Amplification of the Centre of Excellence on Green Chemistry Methods and Processes, CEGreenII) [2640120025]
Several bioactive natural p-hydroxyphenylalkyl beta-D-glucopyranosides, such as vanillyl beta-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, p-O-acetylated arylalkyl alcohols, were prepared by the reduction of the corresponding acetylated aldehydes or acids. Various stereoselective 1,2-trans-O-glycosylation methods were studied, including the DDQ-iodine or ZnO-ZnCl2 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 Zemplen deacetylation.
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