Merging Reagent Modulation and Remote Anchimeric Assistance for Glycosylation: Highly Stereoselective Synthesis of alpha-Glycans up to a 30-mer

doi:10.1002/anie.202103826

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	Merging Reagent Modulation and Remote Anchimeric Assistance for Glycosylation: Highly Stereoselective Synthesis of alpha-Glycans up to a 30-mer
	Zhang,Yunqin ; He,Haiqing ; Chen,Zixi ; Huang,Yingying ; Xiang,Guisheng ; Li,Penghua; Yang,Xingkuan ; Lu,Gang ; Xiao,Guozhi
	2021
发表期刊	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
ISSN	1433-7851
卷号	60 期号:22 页码:12597-12606
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.
关键词	1 2-cis glycosylation reagent modulation remote anchimeric assistance structure elucidation synthetic methods
DOI	10.1002/anie.202103826
WOS记录号	WOS:000643876400001
引用统计
文献类型	期刊论文
条目标识符	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.

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