First Synthesis of Bioactive Diphyllin Glycosides Isolated from Justicia patentiflor Hemsl

The syntheses of three naturally occurring diphyllin glycosides have been achieved. 7-O-β-D-Qtfmovopyranosyldiphyllin （patentiflorin A） and 7-O-β-L-fucopyranosyldiphyllin （patentiflorin B） were synthesized by the glycosylation of diphyllin with peracetylglycosyl bromides under phase transfer catalys...

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Bibliographic Details
Published in:Chinese journal of chemistry 2007-05, Vol.25 (5), p.679-682
Main Author: 赵育 李英霞
Format: Article
Language:English
Subjects:
diphyllin
diphyllin glycoside
glycoside
phase transfer catalysis
synthesis
山荷叶素糖苷
水杨柳
生物活性成分
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Summary:The syntheses of three naturally occurring diphyllin glycosides have been achieved. 7-O-β-D-Qtfmovopyranosyldiphyllin （patentiflorin A） and 7-O-β-L-fucopyranosyldiphyllin （patentiflorin B） were synthesized by the glycosylation of diphyllin with peracetylglycosyl bromides under phase transfer catalysis （PTC） conditions. 4＂-O-Acetyl-7-O-β-L-fucopyranosyldiphyllin （4＂-O-acetyl patentiflorin B） was obtained from patentiflorin B on an orthoesterification-orthoester rearrangement approach. Their ^1H NMR, ^13C NMR and HRMS signals are all consistent with those reported for the natural product.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.200790127