Direct Glycosylation of Bioactive Small Molecules with Glycosyl Iodide and Strained Olefin as Acid Scavenger

doi:10.1021/jo402551x

	Direct Glycosylation of Bioactive Small Molecules with Glycosyl Iodide and Strained Olefin as Acid Scavenger
	Gu, Xiangying 2,3; Chen, Lin 3; Wang, Xin3 ; Liu, Xiao 2,3; You, Qidong 2; Xi, Wenwei 1; Gao, Li 1; Chen, Guohua 2; Chen, Yue-Lei3 ; Xiong, Bing3
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2014-02-07
卷号	79 期号:3 页码:1100-1110
ISSN号	0022-3263
DOI	10.1021/jo402551x
文献子类	Article
英文摘要	A new strategy for diversity-oriented direct glycosylation of bioactive small molecules was developed. This reaction features (-)-beta-pinene as acid scavenger and work with glycosyl iodides under mild conditions. With the aid of RP-HPLC and chiral SFC separation techniques, the new direct glycosylation proved effective at gram scale on bioactive small molecules including AZD6244, podophyllotoxin, paclitaxel, and docetaxel. Interesting glycoside derivatives were efficiently created with good yields and 1,2-cis selectivity.
资助项目	National Natural Science Foundation of China[81102306] ; National Science & Technology Major Project "Key New Drug Creation and Manufacturing Program", China[2012ZX09301001]
WOS关键词	INHIBITING NATURAL SUBSTANCES ; ALPHA-LINKED DISACCHARIDES ; SUGAR BIOSYNTHESIS ; PROTECTIVE GROUPS ; HYDROXY-GROUPS ; CANCER-CELLS ; DERIVATIVES ; BETA ; EFFICIENT ; DONORS
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000331163800028
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/277189]
专题	药物化学研究室
通讯作者	Chen, Guohua
作者单位	1.Shanghai Chiralway Biotech Co Ltd, Shanghai 200237, Peoples R China 2.China Pharmaceut Univ, Sch Pharm, Nanjing 210009, Jiangsu, Peoples R China; 3.Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China;
推荐引用方式 GB/T 7714	Gu, Xiangying,Chen, Lin,Wang, Xin,et al. Direct Glycosylation of Bioactive Small Molecules with Glycosyl Iodide and Strained Olefin as Acid Scavenger[J]. JOURNAL OF ORGANIC CHEMISTRY,2014,79(3):1100-1110.
APA	Gu, Xiangying.,Chen, Lin.,Wang, Xin.,Liu, Xiao.,You, Qidong.,...&Shen, Jingkang.(2014).Direct Glycosylation of Bioactive Small Molecules with Glycosyl Iodide and Strained Olefin as Acid Scavenger.JOURNAL OF ORGANIC CHEMISTRY,79(3),1100-1110.
MLA	Gu, Xiangying,et al."Direct Glycosylation of Bioactive Small Molecules with Glycosyl Iodide and Strained Olefin as Acid Scavenger".JOURNAL OF ORGANIC CHEMISTRY 79.3(2014):1100-1110.