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

页码：5922 / 5933

页数：12

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