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Stereo selectivity investigation on glycosylation of oxazolidinone protected 2-amino-2-deoxy-D-glucose donors based on pre-activation protocol
Geng, Yiqun; Zhang, Li-He; Ye, Xin-Shan
关键词Oxazolidinone Pre-activation Glycosylation Stereoselectivity Carbohydrate
刊名TETRAHEDRON
2008-05-26
DOI10.1016/j.tet.2008.03.103
64期:22页:4949-4958
收录类别SCI ; IC
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Organic
研究领域[WOS]Chemistry
关键词[WOS]POT OLIGOSACCHARIDE SYNTHESIS ; BETA-MANNOPYRANOSIDES ; GLYCOSIDIC LINKAGES ; THIOGLYCOSIDES ; STRATEGY ; DERIVATIVES ; ANHYDRIDE ; PROMOTER ; SUGARS
英文摘要

Diverse 23-oxazolidinone protected 2-amino-2-deoxy-D-glucose thioglycosides were prepared and studied as glycosyl donors at low temperature by BSM/Tf(2)O pre-activation protocol before the addition of glycosyl acceptors. The stereochemistry outcomes of a series of glycosylations were investigated. Different stereoselectivities of the coupling reactions were obtained, arising from the different protecting groups in the oxazolidinone donors. 4,6-Di-O-benzyl-N-benzyl-oxazolidinone protected thioglycoside donor I c underwent glycosylation with general beta-anomeric selectivity and the stereoselectivity could be also affected by glycosylation conditions. (C) 2008 Elsevier Ltd. All rights reserved.

语种英语
WOS记录号WOS:000256179700003
引用统计
被引频次:32[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/51128
专题北京大学药学院
作者单位Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100083, Peoples R China
推荐引用方式
GB/T 7714
Geng, Yiqun,Zhang, Li-He,Ye, Xin-Shan. Stereo selectivity investigation on glycosylation of oxazolidinone protected 2-amino-2-deoxy-D-glucose donors based on pre-activation protocol[J]. TETRAHEDRON,2008,64(22):4949-4958.
APA Geng, Yiqun,Zhang, Li-He,&Ye, Xin-Shan.(2008).Stereo selectivity investigation on glycosylation of oxazolidinone protected 2-amino-2-deoxy-D-glucose donors based on pre-activation protocol.TETRAHEDRON,64(22),4949-4958.
MLA Geng, Yiqun,et al."Stereo selectivity investigation on glycosylation of oxazolidinone protected 2-amino-2-deoxy-D-glucose donors based on pre-activation protocol".TETRAHEDRON 64.22(2008):4949-4958.
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