Synthesis of a Novel UDP-carbasugar as UDP-galactopyranose Mutase Inhibitor

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• 作者：Sandy El Bkassiny ; In猫s N鈥橤o ; Charlotte M. Sevrain ; Abdellatif Tikad ; St茅phane P. Vincent
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：May 2, 2014
• 年：2014
• 卷：16
• 期：9
• 页码：2462-2465
• 全文大小：319K
• 年卷期：v.16,no.9(May 2, 2014)
• ISSN：1523-7052

文摘

The multistep synthesis of a novel UDP-C-cyclohexene, designed as a high energy intermediate analogue of the UDP-galactopyranose mutase (UGM) catalyzed isomerization reaction, is reported. The synthesis of the central carbasugar involved the preparation of a galactitol derivative bearing two olefins necessary for the construction of the cyclohexene ring by a ring-closing metathesis as a key step. Further successive phosphonylation, deprotection, and UMP coupling provided the target molecule. The final molecule was assayed against UGM and compared with UDP-C-Galf, the C-glycosidic UGM substrate analogue.