Reinvestigation of N, N-Diacetylimido-Protected 2-Aminothioglycosides in O-Glycosylation: Intermolecular Hydrogen Bonds Contributing to 1,2-Orthoamide Formation

doi:10.1021/acs.joc.1c01009

	Reinvestigation of N, N-Diacetylimido-Protected 2-Aminothioglycosides in O-Glycosylation: Intermolecular Hydrogen Bonds Contributing to 1,2-Orthoamide Formation
	Shao, Liming 1; Huo, Zhenni 1; Lei, Na 1; Yang, Min2 ; He, Zehuan 1; Zhang, Yongliang 1; Wei, Qinlong 1; Chen, Changsheng 1; Xiao, Mei 1; Wang, Fei 1; Gu, Guofeng 1; Cai, Feng 1
	2021-10-01
发表期刊	JOURNAL OF ORGANIC CHEMISTRY (IF:3.3[JCR-2023],3.2[5-Year])
ISSN	0022-3263
EISSN	1520-6904
卷号	86 期号:19 页码:13212-13230
发表状态	已发表
DOI	10.1021/acs.joc.1c01009
摘要	N,N-Diacetylimido protection of 2-aminoglycosides is an elegant strategy but has had limited applications due to unexpected side reactions in glycosylation. We found that high acid concentrations could diminish the side reactions. We observed intermolecular hydrogen bonding among alcohols and acids could disrupt. Assuming that intermolecular hydrogen bonding accelerates the formation of 1,2-orthoamides and disrupting intermolecular hydrogen bonds could turn to the desired glycosylation, we successfully employed sulfenyl triflate pre-activation in the glycosylation of a broad scope of alcohol acceptors, as well as in a one-pot synthesis of a protected human milk oligosaccharide, lacto-N-neotetraose. ©
关键词	Hydrogen bonds Acid concentrations Aminoglycosides Glycosylations Human milk oligosaccharides Intermolecular hydrogen bonding Intermolecular hydrogen bonds O glycosylation One pot synthesis Side reactions Triflates
收录类别	SCIE ; EI ; IC
语种	英语
WOS研究方向	Chemistry
WOS类目	Chemistry, Organic
WOS记录号	WOS:000704707200004
出版者	American Chemical Society
EI入藏号	20213910958664
EI主题词	Glycosylation
EI分类号	461.9 Biology ; 801.2 Biochemistry ; 801.4 Physical Chemistry
原始文献类型	Journal article (JA)
引用统计	正在获取...
文献类型	期刊论文
条目标识符	https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/133400
专题	物质科学与技术学院_公共科研平台_分析测试平台
通讯作者	Cai, Feng
作者单位	1.National Glycoengineering Research Center and Shandong Provincial, Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, 72 Binhai Road, Qingdao; 266237, China; 2.Center for Analysis and Characterization, School of Physical Science and Technology, ShanghaiTech University, 393 Huaxia Middle Rd., Shanghai; 201210, China
推荐引用方式 GB/T 7714	Shao, Liming,Huo, Zhenni,Lei, Na,et al. Reinvestigation of N, N-Diacetylimido-Protected 2-Aminothioglycosides in O-Glycosylation: Intermolecular Hydrogen Bonds Contributing to 1,2-Orthoamide Formation[J]. JOURNAL OF ORGANIC CHEMISTRY,2021,86(19):13212-13230.
APA	Shao, Liming.,Huo, Zhenni.,Lei, Na.,Yang, Min.,He, Zehuan.,...&Cai, Feng.(2021).Reinvestigation of N, N-Diacetylimido-Protected 2-Aminothioglycosides in O-Glycosylation: Intermolecular Hydrogen Bonds Contributing to 1,2-Orthoamide Formation.JOURNAL OF ORGANIC CHEMISTRY,86(19),13212-13230.
MLA	Shao, Liming,et al."Reinvestigation of N, N-Diacetylimido-Protected 2-Aminothioglycosides in O-Glycosylation: Intermolecular Hydrogen Bonds Contributing to 1,2-Orthoamide Formation".JOURNAL OF ORGANIC CHEMISTRY 86.19(2021):13212-13230.