Synthesis of cyclopropyl glycosides and their use as novel glycosyl donors

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• 作者：Clark Scholl^a ; Thomas Licisyn^a ; Christopher Cummings^a ; Kevin Hughes^a ; David Johnson^b ; Walter Boyko^a ; Robert Giuliano^a ; ^{robert.giuliano@villanova.edu}
• 关键词：Cyclopropyl glycosides ; Serine glycoside ; Threonine glycoside
• 刊名：Carbohydrate Research
• 出版年：2012
• 出版时间：15 July, 2012
• 年：2012
• 卷：356
• 期：Complete
• 页码：288-294
• 全文大小：638 K

文摘

Methods for the synthesis of cyclopropyl glycosides and their use as glycosyl donors are described. Cyclopropyl glycosides containing different substituents were prepared by cyclopropanation of the corresponding vinyl glycosides, or by glycosidation of cyclopropyl alcohols that are synthesized by the Kulinkovich reaction. 1-Methyl- and 1-phenyl-substituted cyclopropyl glycosides undergo coupling to Fmoc-protected serine and threonine and to partially protected monosaccharides in the presence of TMS triflate to give glycosidated products.