Syntheses and reactions of 5-O-acetyl-1,2-anhydro-3-O-benzyl-alpha-D-ribofuranose and -beta-D-lyxofaranose, 5-O-acetyl-1,2-anhydro-3,6-di-O-benzyl- and 1,2-anhydro-5,6-di-O-benzoyl-3-O-benzyl-beta-D-mannofuranose, and 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-alpha-D-glucopyranose and -beta-D-talopyranose
文献类型：期刊论文
| 作者 | Ning, J; Kong, FZ |
| 刊名 | CARBOHYDRATE RESEARCH
 |
| 出版日期 | 2001 |
| 卷号 | 330期号:2页码:165-175 |
| 关键词 | Carbohydrate Furanose 1 Pyranose 2-anhydro Sugars |
| DOI | 10.1016/S0008-6215(00)00290-1 |
| 英文摘要 | The title compounds 5-O-acetyl-1,2-anhydro-3-O-benzyl-alpha -D-ribofuranose and 5-O-acetyl-1,2-anhydro-3-O-benzyl-beta -D-lyxofuranose, and 6-O-acetyl-1,2-auhydro-3,4-di-O-benzyl-alpha -D-glucopyranose and 6-O-acetyl-1,2-anhydro-3,4-diO-benzyl-beta -D-taloypranose, and 5-O-acetyl-1,2-anhydro-3,6-di-O-benzyl-beta -D-mannofuranose and 1,2-anhydro-5,6-di-O-benzoyl-3-O-benzyl-beta -D-mannofuranose have each been synthesized from the corresponding 2-O-tosylate and 1-free hydroxyl inter-mediates by base-initiated intramolecular S(N)2 ring closure in almost quantitative yields. Acetyl and benzoyl groups were not affected in the ring closure reactions. Condensation of 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-alpha -D-glucopyranose and 5-O-acetyl-1,2-anhydro-3,6-di-O-benzyl-beta -D-mannpfuranose with 1,2:3,4-di-O-isopropylidene-alpha -D-galactopyranose in the presence of ZnCl2 as the catalyst afforded the 1,2-trans-linked 6-O-acetyl-3,4-di-O-benzyl-alpha -D-glucopyranosyl-(1-6)-1,2:3,4-di-O-isopropylidene-alpha -D-galactopyranose and 5-O-acetyl-3,6-di-O-benzyl-alpha -O-mannofuranosyl-(1-->6)-1,2:3,4-di-O-isopropylidene-a-D-galactopyranose as the sole products in satisfactory yields, while condensation of 5-O-acetyl-1,2-anhydro-3-O-benzyl-beta -D-lyxofuranose with 3-O-benzyl-1,2-O-isoproyylidene-alpha -D-xylofuranose yielded the 1,2-trans-linked 5-O-acetyl-3-O-benzyl-alpha -D-lyxofuranosyl-(1-->5)-3-O-benzyl-1,3-O-isopropylidene-alpha -D-xylofuranose as the sole product in a good yield. The 6-O-acetyl group in the glycosyl donor, 6-O-acetyl-1,2-anhydro-3,4-di-O-brnzyl-alpha -D-glucopyranose did not influence the stereoselectivity of the ring-opening-coupling, reaction. (C) 2001 Published by Elsevier Science Ltd. All rights reserved. |
| WOS记录号 | WOS:000166805900002 |
| 源URL | [http://ir.rcees.ac.cn/handle/311016/24106]  |
| 专题 | 生态环境研究中心_中国科学院环境生物技术重点实验室 |
| 推荐引用方式 GB/T 7714 | Ning, J,Kong, FZ. Syntheses and reactions of 5-O-acetyl-1,2-anhydro-3-O-benzyl-alpha-D-ribofuranose and -beta-D-lyxofaranose, 5-O-acetyl-1,2-anhydro-3,6-di-O-benzyl- and 1,2-anhydro-5,6-di-O-benzoyl-3-O-benzyl-beta-D-mannofuranose, and 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-alpha-D-glucopyranose and -beta-D-talopyranose[J]. CARBOHYDRATE RESEARCH,2001,330(2):165-175. |
| APA | Ning, J,&Kong, FZ.(2001).Syntheses and reactions of 5-O-acetyl-1,2-anhydro-3-O-benzyl-alpha-D-ribofuranose and -beta-D-lyxofaranose, 5-O-acetyl-1,2-anhydro-3,6-di-O-benzyl- and 1,2-anhydro-5,6-di-O-benzoyl-3-O-benzyl-beta-D-mannofuranose, and 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-alpha-D-glucopyranose and -beta-D-talopyranose.CARBOHYDRATE RESEARCH,330(2),165-175. |
| MLA | Ning, J,et al."Syntheses and reactions of 5-O-acetyl-1,2-anhydro-3-O-benzyl-alpha-D-ribofuranose and -beta-D-lyxofaranose, 5-O-acetyl-1,2-anhydro-3,6-di-O-benzyl- and 1,2-anhydro-5,6-di-O-benzoyl-3-O-benzyl-beta-D-mannofuranose, and 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-alpha-D-glucopyranose and -beta-D-talopyranose".CARBOHYDRATE RESEARCH 330.2(2001):165-175. |
入库方式： OAI收割
来源：生态环境研究中心
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