Stereoselective Synthesis of 1,2-cis-Glycosyl Sulfones and Their Application in One-Pot Julia Olefination for the Synthesis of exo-Glycals

被引：2
|
作者：
Oka, Natsuhisa [1 ,2 ,3 ]
Suzuki, Kanna [1 ]
Mori, Ayumi [1 ]
Ando, Kaori [1 ]
机构：
[1] Gifu Univ, Dept Chem & Biomol Sci, Fac Engn, 1-1 Yanagido, Gifu 5011193, Japan
[2] Gifu Univ G CHAIN, Ctr Highly Adv Integrat Nano & Life Sci, 1-1 Yanagido, Gifu 5011193, Japan
[3] Gifu Univ, Inst Glycocore Res iGCORE, 1-1 Yanagido, Gifu 5011193, Japan
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 2021卷 / 44期
关键词：
Diastereoselectivity; Glycosides; Glycosylation; Olefination; Sulfones; RIBOFURANOSYL IODIDES; 2-PYRIDYL SULFONES; GLYCOSYL IODIDES; C-GLYCOSIDES; THIOGLYCOSIDES; DERIVATIVES; INHIBITORS; 1,2-TRANS-C-GLYCOSIDES; DISACCHARIDES; ACTIVATION;
D O I：
10.1002/ejoc.202101202
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Glycosyl sulfones are important intermediates in the synthesis of various sugar derivatives. However, their 1,2-cis-isomers have not been extensively studied because of lower availability. Herein, we report the highly stereoselective synthesis of heteroaryl-substituted 1,2-cis-glycosyl sulfones via glycosylation of heteroarylthiols and subsequent oxidation by magnesium monoperphthalate. One-pot Julia olefination using these 1,2-cis-glycosyl sulfones was also studied. It furnished thermodynamically less stable (E)-exo-glycals with E/Z selectivity of up to 91 : 9.
引用
收藏
页码：5922 / 5933
页数：12
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