| First Synthesis of a Series of New Natural Glucosides |
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| 引用本文： | 屈孟男 周岭 曹小平. First Synthesis of a Series of New Natural Glucosides[J]. 中国化学, 2006, 24(11): 1625-1630. DOI: 10.1002/cjoc.200690304 |
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| 作者姓名： | 屈孟男 周岭 曹小平 |
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| 作者单位： | State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000, China |
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| 基金项目： | Project supported by the National Natural Science Foundation of China （Nos. 20472025 and QT 20021001）. |
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| 摘 要： | Alkyl glucoside 1 and aryl glycosides 2-4 were highly stereospecifically synthesized over 4-6 steps from commercially available starting materials. The coupling reaction of the acetobromo-α-D-glucose with the unprotective dihydroxy aglycon in the presence of silver oxide, or with aromatic aglycon in the presence of sodium hydroxide produced the key intermediate. Only β-configuration glycosides were formed in this procedure. The synthesis of all these glycosides was reported for the first time.
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| 关 键 词： | 立体合成 芳基β-D-葡萄糖苷 耦合反应 天然葡萄糖苷 |
| 收稿时间： | 2006-01-05 |
| 修稿时间： | 2006-01-052006-03-09 |
First Synthesis of a Series of New Natural Glucosides |
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| QU, Meng-Nan, ZHOU, Ling, CAO, Xiao-Ping. First Synthesis of a Series of New Natural Glucosides[J]. Chinese Journal of Chemistry, 2006, 24(11): 1625-1630. DOI: 10.1002/cjoc.200690304 |
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| Authors: | QU Meng-Nan ZHOU Ling CAO Xiao-Ping |
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| Affiliation: | State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000, China |
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| Abstract: | Alkyl glucoside 1 and aryl glycosides 2 – 4 were highly stereospecifically synthesized over 4–6 steps from commercially available starting materials. The coupling reaction of the acetobromo‐α‐D‐glucose with the unprotective dihydroxy aglycon in the presence of silver oxide, or with aromatic aglycon in the presence of sodium hydroxide produced the key intermediate. Only β‐configuration glycosides were formed in this procedure. The synthesis of all these glycosides was reported for the first time. |
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| Keywords: | stereospecifical synthesis aryl β‐D‐glucopyranoside coupling reaction |
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