| 含O-, S-, N-和C-2,3-不饱和糖苷的合成 |
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| 引用本文： | 赵辉,李珊,陈沛然.含O-, S-, N-和C-2,3-不饱和糖苷的合成[J].合成化学,2016,24(12):1054-1059. |
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| 作者姓名： | 赵辉 李珊 陈沛然 |
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| 作者单位： | 1. 东华大学 化学化工与生物工程学院，上海 201620；2. 中国科学院 上海有机化学研究所 生命有机化学国家重点实验室，上海 200032 |
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| 基金项目： | 国家自然科学基金资助项目(21272305) |
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| 摘 要： | 以3,4,6-三-O-乙酰基-D-葡萄烯糖为原料，(NH4)2S2O8为催化剂，利用Ferrier重排反应制得一系列含O-, S-,N-和C-2,3-不饱和糖苷，其结构经1H NMR， IR和MS（ESI）确证。考察了催化剂及其用量，溶剂和温度对产率的影响。结果表明：在最优条件［反应温度80 ℃，乙腈为溶剂，(NH4)2S2O8为催化剂(1 eq.)］下，3a产率高达83%。
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| 关 键 词： | Ferrier重排 3 4 6-三-O-乙酰基-D-葡萄烯糖 2 3-不饱和糖苷 合成 |
| 收稿时间： | 2016-05-05 |
Synthesis of 2,3-Unsaturated O-, S-, N-, and C-glycosides |
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| ZHAO Hui,LI Shan,CHEN Pei-ran.Synthesis of 2,3-Unsaturated O-, S-, N-, and C-glycosides[J].Chinese Journal of Synthetic Chemistry,2016,24(12):1054-1059. |
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| Authors: | ZHAO Hui LI Shan CHEN Pei-ran |
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| Abstract: | 2 ,3-Unsaturated O-, S-, N-, and C-glycosides were synthesized by Ferrier rearrangement of 3,4, 6-tri-O-acetyl-D-glucal, using ( NH4 )2 S2 O8 as catalyst. The structures were confirmed by 1 H NMR, IR and MS( ESI) . The effects of catalysts and its amount, solvents and reaction temperature were investigated. The results indicated that the yield of 3a was up to 83% under the optimum condi-tions reaction temperature was 80 ℃, acetonitrile as solvent and (NH4)2S2O8 as catalyst (1 eq. )]. |
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| Keywords: | Ferrier rearrangement 3 4 6-tri-oacetyl-D-glucal 2 3-unsaturated glycoside synthesis |
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