Stereoselective Synthesis of 2-C-Branched (Acetylmethyl) Oligosaccharides and Glycoconjugates: Lewis Acid-Catalyzed Glycosylation from 1,2-Cyclopropaneacetylated Sugars
文献类型：期刊论文
| 作者 | Tian, Qiang ; Dong, Liang ; Ma, Xiaofeng ; Xu, Liyan ; Hu, Changwei ; Zou, Wei ; Shao, Huawu |
| 刊名 | JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2011 |
| 卷号 | 76期号:4页码:1045-1053 |
| ISSN号 | 0022-3263 |
| 产权排序 | 1 |
| 通讯作者 | Hu, Changwei ; Shao, Huawu |
| 英文摘要 | 1,2-Cyclopropaneacetylated sugars as glycosyl donors reacted with a series of glycosyl acceptors (monosaccharides, amino acids, and other alcohols) in the presence of Lewis acid to produce oligosaccharides and glycoconjugates containing 2-C-acetylmethylsugars. Galactosyl donor gave good to excellent alpha-selectivities with TMSOTf as a catalyst, whereas galactosyl donor offered moderate to good beta-selectivities when BF3 center dot Et2O was used as a catalyst. However, glucosyl donors produced beta-exclusive selectivity under both conditions. The stereoselectivities of glycosylation depend on the reactivity of donor sugars and Lewis acid catalyst, which effectively dictated the glycosylation pathways. The evidence suggests that galactosyl donors (e.g., 7) can undergo S(N)1 pathway with a strong Lewis acid (TMSOTf) and S(N)2 pathway under BF3 center dot Et2O, whereas the glucosyl donors (e.g., 8 and 10) followed S(N)2 pathway. The stereoselectivity was also consequential to the formation of a C2'-acetal intermediate formed via the 2-C-acetylmethyl group and the anomeric carbonium intermediate in glycosylation. |
| 学科主题 | Chemistry |
| 收录类别 | SCI |
| 资助信息 | Chinese Academy of Sciences; National Science Foundation of China[20972151] |
| 语种 | 英语 |
| WOS记录号 | WOS:000287122600004 |
| 公开日期 | 2012-11-09 |
| 源URL | [http://210.75.237.14/handle/351003/23559]  |
| 专题 | 成都生物研究所_天然产物研究 |
| 推荐引用方式 GB/T 7714 | Tian, Qiang,Dong, Liang,Ma, Xiaofeng,et al. Stereoselective Synthesis of 2-C-Branched (Acetylmethyl) Oligosaccharides and Glycoconjugates: Lewis Acid-Catalyzed Glycosylation from 1,2-Cyclopropaneacetylated Sugars[J]. JOURNAL OF ORGANIC CHEMISTRY,2011,76(4):1045-1053. |
| APA | Tian, Qiang.,Dong, Liang.,Ma, Xiaofeng.,Xu, Liyan.,Hu, Changwei.,...&Shao, Huawu.(2011).Stereoselective Synthesis of 2-C-Branched (Acetylmethyl) Oligosaccharides and Glycoconjugates: Lewis Acid-Catalyzed Glycosylation from 1,2-Cyclopropaneacetylated Sugars.JOURNAL OF ORGANIC CHEMISTRY,76(4),1045-1053. |
| MLA | Tian, Qiang,et al."Stereoselective Synthesis of 2-C-Branched (Acetylmethyl) Oligosaccharides and Glycoconjugates: Lewis Acid-Catalyzed Glycosylation from 1,2-Cyclopropaneacetylated Sugars".JOURNAL OF ORGANIC CHEMISTRY 76.4(2011):1045-1053. |
入库方式： OAI收割
来源：成都生物研究所
浏览0
下载0
收藏0
其他版本
除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。