A simple, efficient alternative for highly stereoselective iodoacetoxylation of protected glycals

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• 作者：Gammon ; David W. ; Kinfe ; Henok H. ; De Vos ; Dirk E. ; Jacobs ; Pierre A. ; Sels ; Bert F.
• 关键词：Glycals ; 2-Iodoglycosides ; Iodoacetates
• 刊名：Tetrahedron Letters
• 出版年：2004
• 出版时间：December 20, 2004
• 年：2004
• 卷：45
• 期：52
• 页码：9533-9536
• 全文大小：264 K

文摘

Protected glycals are converted in high yields and selectivities in less than 2h at low temperatures to 2-deoxy-2-iodoglycosyl acetates using the simple, inexpensive reagent mixture of ammonium iodide, hydrogen peroxide and acetic anhydride/acetic acid in acetonitrile. The corresponding 2-deoxy-2-bromoglycosyl acetates are obtained using ammonium bromide instead of the iodide, although longer reaction times are required and selectivities are inferior.