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学科主题: 药学
题名:
Additive-Controlled Stereoselective Glycosylations of Oxazolidinone-Protected Glucosamine and Galactosamine Thioglycoside Donors Based on Preactivation Protocol
作者: Geng, Yiqun; Ye, Xin-Shan1
关键词: glycosylation ; stereoselectivity ; preactivation ; additive ; carbohydrate
刊名: SYNLETT
发表日期: 2010-10-01
DOI: 10.1055/s-0030-1258557
期: 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
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
项目资助者: National Natural Science Foundation of China ; Ministry of Science and Technology of China
WOS记录号: WOS:000282091600030
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/55899
Appears in Collections:北京大学药学院_期刊论文

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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

Recommended Citation:
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.
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