Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 16, Pages 3910-3917Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201604955
Keywords
epoxides; glycosylation; nucleosides; riboses; synthesis design
Categories
Funding
- ASCR [RVO: 61388963]
- ASCR (Praemium Academiae)
- Technology Agency of the Czech Republic [TE01020028]
- Czech Science Foundation [16-00178S]
- Gilead Sciences, Inc.
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Simplifying access to synthetic nucleosides is of interest due to their widespread use as biochemical or anticancer and antiviral agents. Herein, a direct stereoselective method to access an expansive range of both natural and synthetic nucleosides up to a gram scale, through direct glycosylation of nucleobases with 5-O-tritylribose and other C5-modified ribose derivatives, is discussed in detail. The reaction proceeds through nucleophilic epoxide ring opening of an in situ formed 1,2-anhydrosugar (termed anhydrose) under modified Mitsunobu reaction conditions. The scope of the reaction in the synthesis of diverse nucleosides and other 1-substituted riboside derivatives is described. In addition, a mechanistic insight into the formation of this key glycosyl donor intermediate is provided.
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