Construction of beta-Mannosidic Bonds via Gold(I)-Catalyzed Glycosylations with Mannopyranosyl ortho-Hexynylbenzoates and Its Application in Synthesis of Acremomannolipin A

doi:10.1021/acs.joc.5b00140

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	Construction of beta-Mannosidic Bonds via Gold(I)-Catalyzed Glycosylations with Mannopyranosyl ortho-Hexynylbenzoates and Its Application in Synthesis of Acremomannolipin A
	Sun, Peng 1; Wang, Peng 1; Zhang, Yongzhen 1; Zhang, Xiuli 1; Wang, Cong 1; Liu, Shaojing 1; Lu, Jinjie 1; Li, Ming1,2
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2015-04-17
卷号	80 期号:8 页码:4164-4175
ISSN号	0022-3263
DOI	10.1021/acs.joc.5b00140
文献子类	Article
英文摘要	A mild and convenient protocol for direct synthesis of beta-mannosides has been developed. Glycosylation of 4,6-O-benzylidene-protected mannosyl ortho-hexynylbenzoates with various alcohol acceptors catalyzed by gold(I) complex proceeded smoothly at 0 degrees C to room temperature and afforded the corresponding beta-mannoside in high yield and satisfactory stereoselectivity. This reaction was applied to the total synthesis of acremomannolipin A and its analogue.
资助项目	National Science Funding of China[21272220] ; State key Laboratory of Drug Research[SIMM1403KF-12] ; NSFC-Shandong Joint Fund[U1406402] ; Project on Scientific development in Shangdong Province[2012GHY11526]
WOS关键词	CHARACTERISTIC GLYCOLIPID STRUCTURE ; FUNGUS ACREMONIUM-STRICTUM ; CALCIUM SIGNAL MODULATOR ; ORTHO-ALKYNYLBENZOATES ; SELECTIVE MANNOSYLATION ; CHEMICAL GLYCOSYLATION ; STEREOSELECTIVE-SYNTHESIS ; EFFICIENT GLYCOSYLATION ; O-ALKYNYLBENZOATES ; PROTECTING GROUPS
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000353315000047
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/276570]
专题	药物安全性评价中心中科院受体结构与功能重点实验室新药研究国家重点实验室
通讯作者	Li, Ming
作者单位	1.Ocean Univ China, Sch Med & Pharm, Chinese Minist Educ, Key Lab Marine Med, Qingdao 266003, Shandong, Peoples R China; 2.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
推荐引用方式 GB/T 7714	Sun, Peng,Wang, Peng,Zhang, Yongzhen,et al. Construction of beta-Mannosidic Bonds via Gold(I)-Catalyzed Glycosylations with Mannopyranosyl ortho-Hexynylbenzoates and Its Application in Synthesis of Acremomannolipin A[J]. JOURNAL OF ORGANIC CHEMISTRY,2015,80(8):4164-4175.
APA	Sun, Peng.,Wang, Peng.,Zhang, Yongzhen.,Zhang, Xiuli.,Wang, Cong.,...&Li, Ming.(2015).Construction of beta-Mannosidic Bonds via Gold(I)-Catalyzed Glycosylations with Mannopyranosyl ortho-Hexynylbenzoates and Its Application in Synthesis of Acremomannolipin A.JOURNAL OF ORGANIC CHEMISTRY,80(8),4164-4175.
MLA	Sun, Peng,et al."Construction of beta-Mannosidic Bonds via Gold(I)-Catalyzed Glycosylations with Mannopyranosyl ortho-Hexynylbenzoates and Its Application in Synthesis of Acremomannolipin A".JOURNAL OF ORGANIC CHEMISTRY 80.8(2015):4164-4175.