期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 38, 页码 16074-16079出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja307797x
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资金
- Academia Sinica
- National Tsing Hua University
- National Science Council in Taiwan
A new approach for the synthesis of S-linked alpha(2 -> 8) and alternating alpha(2 -> 8)/alpha(2 -> 9) oligosialic acids by S-alkylation has been developed, using chemo- and stereoselective alkylation of a C2-thiolated sialoside donor (nucleophile) with either a C8- or C9-iodide-activated sialoside acceptor (electrophile). An efficient intramolecular acetyl group migration from the C7 to C9-position of the sialoside under mild basic conditions was used to generate the C8-iodide, the key sialyl acceptor (electrophile). Using this strategy, the syntheses of S-linked alpha(2 -> 8) and alpha(2 -> 8)/alpha(2 -> 9) hexasialic acids were achieved.
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