Merging Reagent Modulation and Remote Anchimeric Assistance for Glycosylation: Highly Stereoselective Synthesis of alpha-Glycans up to a 30-mer
文献类型：期刊论文
| 作者 | Zhang,Yunqin; He,Haiqing; Chen,Zixi; Huang,Yingying; Xiang,Guisheng; Li,Penghua ; Yang,Xingkuan; Lu,Gang; Xiao,Guozhi
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| 刊名 | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
 |
| 出版日期 | 2021 |
| 卷号 | 60期号:22页码:12597-12606 |
| 关键词 | 1 2-cis glycosylation reagent modulation remote anchimeric assistance structure elucidation synthetic methods |
| ISSN号 | 1433-7851 |
| DOI | 10.1002/anie.202103826 |
| 英文摘要 | The efficient synthesis of long, branched, and complex carbohydrates containing multiple 1,2-cis glycosidic linkages is a long-standing challenge. Here, we report a merging reagent modulation and 6-O-levulinoyl remote anchimeric assistance glycosylation strategy, which is successfully applied to the first highly stereoselective synthesis of the branched Dendrobium Huoshanense glycans and the linear Longan glycans containing up to 30 contiguous 1,2-cis glucosidic bonds. DFT calculations shed light on the origin of the much higher stereoselectivities of 1,2-cis glucosylation with 6-O-levulinoyl group than 6-O-acetyl or 6-O-benzoyl groups. Orthogonal one-pot glycosylation strategy based on glycosyl ortho-alkynylbenzoates and ortho-(1-phenylvinyl)benzoates has been demonstrated in the efficient synthesis of complex glycans, precluding such issues as aglycon transfer inherent to orthogonal one-pot synthesis based on thioglycosides. |
| WOS记录号 | WOS:000643876400001 |
| 源URL | [http://ir.kib.ac.cn/handle/151853/73191]  |
| 专题 | 中国科学院昆明植物研究所 |
| 作者单位 | 1.Univ Chinese Acad Sci, Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, 132 Lanhei Rd, Kunming 650201, Yunnan, Peoples R China 2.Shandong Univ, Sch Chem & Chem Engn, Key Lab Colloid & Interface Chem, State Key Lab Crystal Mat,Minist Educ, Jinan 250100, Shandong, Peoples R China |
| 推荐引用方式 GB/T 7714 | Zhang,Yunqin,He,Haiqing,Chen,Zixi,et al. Merging Reagent Modulation and Remote Anchimeric Assistance for Glycosylation: Highly Stereoselective Synthesis of alpha-Glycans up to a 30-mer[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2021,60(22):12597-12606. |
| APA | Zhang,Yunqin.,He,Haiqing.,Chen,Zixi.,Huang,Yingying.,Xiang,Guisheng.,...&Xiao,Guozhi.(2021).Merging Reagent Modulation and Remote Anchimeric Assistance for Glycosylation: Highly Stereoselective Synthesis of alpha-Glycans up to a 30-mer.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,60(22),12597-12606. |
| MLA | Zhang,Yunqin,et al."Merging Reagent Modulation and Remote Anchimeric Assistance for Glycosylation: Highly Stereoselective Synthesis of alpha-Glycans up to a 30-mer".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 60.22(2021):12597-12606. |
入库方式： OAI收割
来源：昆明植物研究所
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