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CHEMICAL PAPERS · 2014 ·Vol. 68 ·期 8 ·1132-1136 · IF 1.193

Efficient one-pot synthesis of 2-hydroxyethyl per-O-acetyl glycosides

Tao Hong-Wen,Wang Xia,Yi Ping-Gui,Deng Zhi-Hong,Yu Xian-Yong,Li Xiao-Fang

A class of stereo-isomerically-pure alkanediol monoglycosides, 2-hydroxyethyl per- O -acetyl pyranosides ( IIIa-IIIf ), was conveniently prepared by a one-pot reaction of per- O -acetylated pyranoses ( Ia-If ) and 2-( tert -butyldimethylsilyloxy)ethanol ( II ) with catalysis by BF 3 ·OEt 2 . The α -( IIIa ) or β -linked glycosides ( IIIb-IIIf ) with 1,2- trans -configuration were obtained from glycosyl donors with participation of the neighbouring 2- O -acetyl group. BF 3 ·OEt 2 , along with hydrogen fluoride released from BF 3 ·OEt 2 under the experimental conditions used, facilitates the subsequent de-protection of siloxane to successfully afford 2-hydroxyethyl per- O -acetyl-pyranosides.

研究领域: 有机化学 · 糖化学

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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY · 2013 ·Vol. 2013 ·期 32 ·7411-7420 · IF 3.344

BF3·OEt2-Promoted Tandem O-Arylation/Hydroxylation: Efficient Synthesis of 2-Hydroxyflavanones from Triazenylaryl-Substituted Diketones

Zhengkai Chen,Weijun Yang,Lijun Xu,Lili Zhang,Maozhong Miao,Hongjun Ren

Graphical Highly substituted 2-hydroxyflavanones can be obtained through a tandem O -arylation/hydroxylation process from triazenylaryl-substituted diketones in the presence of a Lewis acid. A transition-metal-free tandem O -arylation/hydroxylation approach has been developed for the efficient synthesis of highly substituted 2-hydroxyflavanones from triazenylaryl-substituted diketones. The intermediate benzopyrylium cation may be involved in these reactions.

研究领域: 有机化学 · 药物化学

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Efficient one-pot synthesis of 2-hydroxyethyl per-O-acetyl glycosides

BF3·OEt2-Promoted Tandem O-Arylation/Hydroxylation: Efficient Synthesis of 2-Hydroxyflavanones from Triazenylaryl-Substituted Diketones