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Additive-Controlled Stereoselective Glycosylations of Oxazolidinone-Protected Glucosamine and Galactosamine Thioglycoside Donors Based on Preactivation Protocol
Geng, Yiqun; Ye, Xin-Shan1
关键词Glycosylation Stereoselectivity Preactivation Additive Carbohydrate
刊名SYNLETT
2010-10-01
DOI10.1055/s-0030-1258557
16页:2506-2512
收录类别SCI ; IC
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Organic
资助者National Natural Science Foundation of China ; Ministry of Science and Technology of China ; National Natural Science Foundation of China ; Ministry of Science and Technology of China
研究领域[WOS]Chemistry
关键词[WOS]OLIGOSACCHARIDE SYNTHESIS ; BETA-MANNOPYRANOSIDES ; SULFOXIDE METHOD ; SULFONIUM IONS ; POT ; STRATEGY ; GLYCOSIDATION ; DERIVATIVES ; CHEMISTRY
英文摘要

Based on a pre-activation protocol, the stereoselectivity of oxazolidinone-protected amino sugar thioglycoside donors towards glycosylations can be controlled by additives. Either alpha-or beta-selectivity could be obtained by changing additives. 2,4,6-Tri-tert-butylpyrimidine (TTBP) was the best beta-directing additive, while thiophene worked as the best alpha-directing additive. The bifunctional additives such as tetrabutyl ammonium iodide (TBAI) afforded either alpha-or beta-selectivity depending on the amount added. Poor alpha-selectivity of some glycosylations without any additives was greatly improved by adding TBAI or thiophene.

语种英语
所属项目编号20732001 ; 2009ZX09501-011
资助者National Natural Science Foundation of China ; Ministry of Science and Technology of China ; National Natural Science Foundation of China ; Ministry of Science and Technology of China
WOS记录号WOS:000282091600030
引用统计
被引频次:17[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/400002259/55899
专题北京大学药学院
作者单位1.Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
2.Peking Univ, Sch Pharmaceut Sci, Beijing 100191, Peoples R China
推荐引用方式
GB/T 7714
Geng, Yiqun,Ye, Xin-Shan. Additive-Controlled Stereoselective Glycosylations of Oxazolidinone-Protected Glucosamine and Galactosamine Thioglycoside Donors Based on Preactivation Protocol[J]. SYNLETT,2010(16):2506-2512.
APA Geng, Yiqun,&Ye, Xin-Shan.(2010).Additive-Controlled Stereoselective Glycosylations of Oxazolidinone-Protected Glucosamine and Galactosamine Thioglycoside Donors Based on Preactivation Protocol.SYNLETT(16),2506-2512.
MLA Geng, Yiqun,et al."Additive-Controlled Stereoselective Glycosylations of Oxazolidinone-Protected Glucosamine and Galactosamine Thioglycoside Donors Based on Preactivation Protocol".SYNLETT .16(2010):2506-2512.
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