期刊
CHEMISTRY-AN ASIAN JOURNAL
卷 4, 期 7, 页码 1114-1125出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.200800448
关键词
glycosides; glycosylation; iodine; oxidative activation; synthetic methods
资金
- NEDO (New Energy and Industrial Technology Development Organization)
- JSPS
Efficient synthesis of the deoxysugar part of versipelostatin (VST) was achieved by direct and stereoselective glycosylation of the reduced VST aglycon. Activation of 2-deoxyglycosyl imidate with IBr under basic conditions enables alpha-selective glycosylation of beta-2-deoxylglycosides without anomerization. Comparison of the synthetic and natural VST products using NMR indicates that versipelostatin has a beta-D-digitoxose-(1,4)-alpha-L-oleandrose-(1,4)-beta-D-digitoxose trisaccharide. In addition, results of a biological assay indicate that the deoxyoligosaccharide unit of the synthetic glycoside was important for biological activity of the compound.
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