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Stereoselective Phenylselenoglycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides.
Organic Letters ( IF 5.2 ) Pub Date : 2020-03-27 , DOI: 10.1021/acs.orglett.0c00732
Shuai Meng 1 , Wenhe Zhong 1 , Wang Yao 1 , Zhongjun Li 1
Affiliation  

A phenylselenoglycosylation reaction of glycal derivatives mediated by diphenyl diselenide and phenyliodine(III) bis(trifluoroacetate) under mild conditions is described. Stereoselective glycosylation has been achieved by installing fused carbonate on those glycals. 3,4-O-Carbonate galactals and 2,3-O-carbonate 2-hydroxyglucals are converted into corresponding glycosides in good yields with excellent β-selectivity, resulting in 2-phenylseleno-2-deoxy-β-galactosides and 2-phenylseleno-β-mannosides which are good precursors of 2-deoxy-β-galactosides and β-mannosides, respectively.

中文翻译:

带有熔融碳酸盐部分的乙二醇的立体选择性苯基硒代糖基化,用于合成2-脱氧-β-半乳糖苷和β-甘露糖苷。

描述了在温和条件下由二苯基二硒化物和苯基碘(III)双(三氟乙酸酯)介导的糖衍生物的苯基硒糖基化反应。立体选择性糖基化反应是通过在这些糖基上安装熔融碳酸盐来实现的。3,4- ø -碳酸酯galactals和2,3- ö -碳酸酯2- hydroxyglucals被转换成对应于良好的产率具有优良的β选择性糖苷,产生2- phenylseleno -2-脱氧-β半乳糖苷和2- phenylseleno -β-甘露糖苷分别是2-脱氧-β-半乳糖苷和β-甘露糖苷的良好前体。
更新日期:2020-04-24
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