- Glycosylation initiated cationic ring-opening polymerization of tetrahydrofuran to prepare neo-glycopolymers
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An unprecedented and highly efficient glycosylation initiated cationic ring-opening polymerization (CROP) of tetrahydrofuran is disclosed employing glycosyl ortho-hexynylbenzoates as donors and gold(i) as a catalyst, that provides an easy access to novel glycopolymers which could self-assemble into nanostructures.
- Li, Yao,Yu, Biao
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supporting information; experimental part
p. 6060 - 6062
(2010/11/02)
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- Synthesis of kaempferol 3- O -(3″,6″-Di- O - E - p -coumaroyl)-β- D -glucopyranoside, efficient glycosylation of flavonol 3-OH with glycosyl o -alkynylbenzoates as donors
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Kaempferol 3-O-(3″,6″-di-O-E-p-coumaroyl)-β-d- glucopyranoside (1), an optimal metabolite of Scots pine seedlings for protection of deep-lying tissue against damaging UV-B, represents a typical acylated flavonol 3-O-glycoside. This compound was synthesized for the first time via two approaches. The first approach, starting with kaempferol, featured formation of the flavonol 3-O-glycosidic linkage with a glycosyl bromide under conventional PTC conditions. In the second approach, 5,7,4′-tri-O-benzyl- kaempferol was readily prepared from 2′,4′,6′- trihydroxyacetophenone and p-hydroxybenzoic acid, which was coupled with a glucopyranosyl o-hexynylbenzoate under the catalysis of a gold(I) complex to provide the desired 3-O-glycoside in excellent yield. A variety of the glycosyl o-hexanylbenzoates equipped with the 2-O-benzoyl group were also proven to be highly efficient donors for construction of the flavonol 3-O-glycosidic linkages.
- Yang, Weizhun,Sun, Jiansong,Lu, Wenxiang,Li, Yan,Shan, Lei,Han, Wei,Zhang, Wei-Dong,Yu, Biao
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experimental part
p. 6879 - 6888
(2010/11/24)
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