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Please use this identifier to cite or link to this item:
http://ir.ncue.edu.tw/ir/handle/987654321/15027
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| Title: | Stereoselective Synthesis of Dioxabicycles from 1-C-allyl-2-O-benzyl-glycosides — An Intramolecular Cyclization between 2-O-benzyl Oxygen and the Allyl Double Bond |
| Authors: | Wu, An-Tai;Yi, Tian;Shao, Huawu;Wu, Shih-Hsiung;Zou, Wei |
| Contributors: | 化學系 |
| Date: | 2006-12
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| Issue Date: | 2013-01-07T01:47:36Z
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| Publisher: | Canadian Science Publishing |
| Abstract: | Addition of a proton to the double bond of 1-C-allyl-O-benzylglycosides gave a 2′-carbonium ion, which in turn reacted intramolecularly, in a regio- and diastereo-selective manner, with the nucleophilic oxygen of the 2-O-benzyl group to form an oxonium intermediate. Subsequent cleavage of the benzyl CO bond led to dioxabicycles in moderate yields. Surprisingly, opposite diastereoselectivities were observed from 1-C-allylglycofuranosides and 1-C-allylglycopyranosides, which produced 2,2′-trans- and 2,2′-cis-dioxabicycles, respectively.Key words: C-glycoside, olefin, cyclization, oxocarbonium, dioxabicycles. |
| Relation: | Can. J. Chem., 84(4): 597-602 |
| Appears in Collections: | [化學系] 期刊論文
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| 2020401110007.pdf | 65Kb | Adobe PDF | 441 | View/Open |
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