Synthesis of a chlorogenin glycoside library using an orthogonal protecting group strategy
Naturally occurring spirostanol saponins bear a chacotriose, α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→4)] -β-d-glucopyranose residue as the oligosaccharide moiety which is believed to be important for biological activity. Herein the development of a concise, combinatorial method for the synthesis of two series of glycan variants at the 2′ and/or 4′ positions of chacotriose is described and the structure-activity relationships of the glycone part at 3-OH of chlorogenin investigated. These compounds were found to be weakly-cytotoxic toward leukemia cell lines CCRF and HL-20, indicating that the chacotriose moiety is important for anticancer activity.
Glycosyl N-tosyl benzimidate as a new building block for chemical glycosylation
Seven novel glycosyl N-tosyl benzimidates were prepared by the reactions of the corresponding hemiacetals with imidoyl chloride in 55-88% yields, which were smoothly converted to glycosides, upon treatment with alcohols and catalytic TMSOTf, in 57-99% yields. Georg Thieme Verlag Stuttgart · New York.
Liu, Shaojing,Peng, Yannan,Wang, Peng,Li, Ming
p. 1501 - 1504
(2012/07/27)
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