Stereoselective Synthesis of O-Glycosides with Borate Acceptors

被引：7

作者：

Zhao, Xiaoxiao ^{[1
]}

Zhang, Zhentao ^{[1
]}

Xu, Jing ^{[1
]}

Wang, Nengzhong ^{[1
]}

Huang, Nianyu ^{[1
]}

Yao, Hui ^{[1
]}

机构：

[1] China Three Gorges Univ, Coll Biol & Pharmaceut Sci, Hubei Key Lab Nat Prod Res & Dev, Key Lab Funct Yeast,China Natl Light Ind, Yichang 443002, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 16期

基金：

中国国家自然科学基金; 湖北省教育厅重点项目;

关键词：

C-ARYL GLYCOSIDES; DE-NOVO SYNTHESIS; CATALYTIC SYNTHESIS; GLYCOSYLATION; REARRANGEMENT; ALKYLATION; REACTIVITY; MILD;

D O I：

10.1021/acs.joc.3c01011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Borate esters have been applied widely as coupling partnersinorganic synthesis. However, the direct utilization of borate acceptorsin O-glycosylation with glycal donors remains underexplored.Herein, we describe a novel O-glycosylation resultingin the formation of 2,3-unsaturated O-glycosidesand 2-deoxy O-glycosides mediated by palladium andcopper catalysis, respectively. This O-glycosylationmethod tolerated a broad scope of trialkyl/triaryl borates and variousglycals with exclusive stereoselectivities in high yields. All thedesired aliphatic/aromatic O-glycosides and 2-deoxy O-glycosides were generated successfully, without the hemiacetalbyproducts and O & RARR;C rearrangement because of the nature of borateesters. The utility of this strategy was demonstrated by functionalizingthe 2,3-unsaturated glycoside products to form saturated & beta;-O-glycosides, 2,3-deoxy O-glycosides, and2,3-epoxy O-glycosides.

引用

页码：11735 / 11747

页数：13

共 60 条

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