Highly Diastereoselective Synthesis of (2'S)-[2'-2H]-2'-Deoxyribonucleosides from the Corresponding Ribonucleosides
- 1 May 1995
- journal article
- research article
- Published by Taylor & Francis in Nucleosides, Nucleotides and Nucleic Acids
- Vol. 14 (3) , 333-336
- https://doi.org/10.1080/15257779508012375
Abstract
The four (2′S)-[2′-2H]-2′-deoxynucleosides (>90 atom % 2H), were synthesized from the corresponding ribonucleosides involving six steps of reactions, i.e., oxidation of their 2′-hydroxyl group, stereoselective reductive deuteration of the resulting 2′-ketonucleoside intermediates with NaB2H4 in EtOH-H2O or EtOH, triflation, bromination with LiBr, highly stereoselective Bu3SnH-Et3B reduction of the resulting bromide, and, finally, unmasking.Keywords
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