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学科主题: 生命有机化学
题名: 1→2Migration and concurrent glycosidation of phenyl 1-thio-α-mannopyranosides via 2,3-O-cyclic dioxonium intermediates
其他题名: 通过2,3-O-cyclic dioxonium中间体的苯硫基吡喃甘露糖苷1-2位的迁移和同时进行的糖苷化反应
作者: Yang ZY(杨尊义) ; Cao HZ(曹鸿志) ; Hu J(胡杰) ; Dan RL(单人立) ; Yu B(俞飚)
通讯作者: 俞飚
刊名: Tetrahedron
发表日期: 2003-01-01
卷: 59, 期:2, 页:249-254
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所生命有机国家重点实验室; 上海大学goodway化学联合研究中心
英文摘要: Treatment of phenyl 2,3-O-cyclic ketene acetal- and 2,3-O-thionocarbonyl-1-thio-mannopyranosides with TMSOTf and MeOTf, respectively, gave the cooesponding 2,3-O-cyclic dioxonium intermediates, which proceeded via I-'2 migration and concuuent glycosidation in the presence of alcohols to provide the conesponding 2-S-phenyl glycosides stereoselectively. While the former donors were too labile, the latter donors have proved superior for the present purpose. The X-ray crystallographic structures of phenyl 4-0-methyl-2,3-O-thiocarbonyl-l-thio-a-L-rhamnopyranoside (l), a typical donor for the present reaction, and its anomeric azide analogue (6), which could not undergo the present reaction under similar conditions, are provided.
语种: 英语
相关网址: 查看原文
内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/18961
Appears in Collections:生命有机化学国家重点实验室_期刊论文

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Recommended Citation:
Yang ZY,Cao HZ,Hu J,et al. 1→2Migration and concurrent glycosidation of phenyl 1-thio-α-mannopyranosides via 2,3-O-cyclic dioxonium intermediates[J]. Tetrahedron,2003,59(2):249-254.
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