Synthesis of 1, 6-anhydro sugars catalyzed by silica supported perchloric acid

Y Chun, S Yan, X Li, N Ding, W Zhang, P Wang, M Li…

Index: Chun, Yuexing; Yan, Shiqiang; Li, Xiangpeng; Ding, Ning; Zhang, Wei; Wang, Peng; Li, Ming; Li, Yingxia Tetrahedron Letters, 2011 , vol. 52, # 46 p. 6196 - 6198

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Citation Number: 9

Abstract

Our initial efforts were directed toward the removal of silyl protecting groups from the carbohydrate building blocks by using HClO 4 ·SiO 2 . For example, to a solution of compound 1 in acetonitrile 20 mol % HClO 4 ·SiO 2 was added and the mixture was stirred for 1.5 h. But interestingly, beside the expected desilylated product 1b (88%), 1,6-anhydro sugar 1a (8%) was obtained as well (Scheme 1). This observation inspired us to try the preparation of 1,6-anhydro sugars by ...