Stereoselective Phenylselenoglycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides.
Stereoselective Phenylselenoglycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides.
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DOI：
10.1021/acs.orglett.0c00732
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发表时间：
2020-03
期刊：
影响因子：
5.2
通讯作者：
Shuai Meng;W. Zhong;Wang Yao;Zhongjun Li
中科院分区：
文献类型：
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作者：
Shuai Meng;W. Zhong;Wang Yao;Zhongjun Li
本文报道了在温和条件下，二苯二硒醚和苯基碘（Ⅲ）二（三氟乙酸盐）介导的糖衍生物的苯基硒糖基化反应。通过在这些糖基上安装稠合碳酸酯，已经实现了立体选择性糖基化。3，4-O-碳酸半乳糖醛和2，3-O-碳酸2-羟基葡糖醛以良好的产率和优异的β-选择性转化为相应的糖苷，得到2-苯硒基-2-脱氧-β-半乳糖苷和2-苯硒基-β-甘露糖苷，它们分别是2-脱氧-β-半乳糖苷和β-甘露糖苷的良好前体。
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.