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

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• 作者：Xiangying Gu ; Lin Chen ; Xin Wang ; Xiao Liu ; Qidong You ; Wenwei Xi ; Li Gao ; Guohua Chen ; Yue-Lei Chen ; Bing Xiong ; Jingkang Shen
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：February 7, 2014
• 年：2014
• 卷：79
• 期：3
• 页码：1100-1110
• 全文大小：493K
• ISSN：1520-6904

文摘

A new strategy for diversity-oriented direct glycosylation of bioactive small molecules was developed. This reaction features (鈭?-尾-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.