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Ferrier Reaction: The first synthesis of 2,3-unsaturated seleno-glycosides by using alkyl(aryl) hydroselenides as the nucleophile and Hf(OTf)4 as the catalyst
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2019-01-03 , DOI: 10.1016/j.tetlet.2019.01.002
Peiran Chen , Yajun Ding , Saisai Guo , Xiaoying Zhang

By using Hf(OTf)4 as the catalyst, a series of 2,3-unsaturated-Se-glucosides have been synthesized for the first time from tri-O-acetyl-d-glucal, 2,4,6-tri-O-benzyl-d-glucal, 3,4-di-O-acetyl-l-rhamnal and ((2R,3S)-3-acetoxy-2,3-dihydrofuran-2-yl) methyl acetate with PhSeH or alkyl(aryl) hydroselenides as the nucleophile in good yield and high anomeric selectivity.



中文翻译:

转移反应:以烷基(芳基)氢硒化物为亲核试剂,以Hf(OTf)4为催化剂,首次合成2,3-不饱和硒代糖苷

通过使用HF(OTF)4作为催化剂,一系列2,3- unsaturated--glucosides已经合成首次从三ö乙酰基d -glucal,2,4,6-三- ö苄基d -glucal,3,4-二- ö乙酰基-rhamnal和((2 - [R,3小号)-3-乙酰氧基-2,3-二氢呋喃-2-基)甲基乙酸酯与PhSeH或烷基(芳基)氢硒化物作为亲核试剂,收率高,端基异构体选择性高。

更新日期:2019-01-03
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