Nucleic Acid Related Compounds. LXXXI. Efficient General Synthesis of Purine (Amino,Azido, and Triflate)-Sugar Nucleosides |
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| Authors: | Morris J. Robins S. D. Hawrelak Amelia E. Hernández Stanislaw F. Wnuk |
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| Affiliation: | 1. Departments of Chemistry , Brigham Young University , Provo, UT, 84602, U.S.A.;2. University of Alberta , Edmonton, Alberta, Canada |
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| Abstract: | Abstract Treatment of 3′,5′-O-(tetraisopropyldisiloxanyl)adenosine and its arabino epimer with trifluoromethanesulfonyl chloride/DMAP gave the 2′-triflates in high yields. Displacements (LiN3/DMF) and deprotection gave 2′-azido-2′-deoxyadenosine and its arabino epimer which were reduced with Bu3SnH/AIBN/DMAC/benzene (or Staudinger reduction) to give 2′-amino-2′-deoxyadenosine and its epimer. Oxidation of 2′,5′-bis-O-(tert-butyldimethylsilyl)adenosine, stereoselective reduction, triflation, azide displacement, deprotection, and reduction gave 3′-amino-3′-deoxyadenosine. |
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