Nucleic Acid Related Compounds. LXXXI. Efficient General Synthesis of Purine (Amino, Azido, and Triflate)-Sugar Nucleosides
- 1 February 1992
- journal article
- research article
- Published by Taylor & Francis in Nucleosides and Nucleotides
- Vol. 11 (2-4) , 821-834
- https://doi.org/10.1080/07328319208021743
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.Keywords
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