期刊
TETRAHEDRON LETTERS
卷 50, 期 45, 页码 6150-6153出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.08.071
关键词
Gangliosides; Sialic acid; Glycosylation; Acanthaster planci
资金
- Japan Society for the Promotion of Science [20710171]
- the Ministry of Education, Culture, Sports, Science, and Technology of Japan
- Grants-in-Aid for Scientific Research [20710171] Funding Source: KAKEN
This Letter reports the first synthesis of the AG2 pentasaccharide, using silylene-oxazolidinone double-locked sialic acid building blocks. The di-DTBS-protected sialic acid building block was easily prepared and readily activated with NIS and TfOH to provide the sialylated lactose unit in good yield with moderate selectivity. After obtaining the trisaccharide unit, the oxazolidinone-protected C4-OH on the sialic acid residue was readily deprotected by treatment with NaOMe. Coupling with the galactofuranosyl beta(1-3)galactopyranosyl fluoride building block produced the desired AG2 pentasaccharide in a highly stereoselective manner. Finally, the desired AG2 pentasaccharide was obtained in good yield following global deprotection. (C) 2009 Elsevier Ltd. All rights reserved.
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