Formation of an Unexpected 2-Deoxy-α-D-Threo-Pentofuranosyl Azide by Reaction of O2,3′-Anhydro-5′-O-trityl-2′-deoxycytidine with Lithium Azide
- 1 February 1992
- journal article
- research article
- Published by Taylor & Francis in Nucleosides and Nucleotides
- Vol. 11 (2-4) , 273-278
- https://doi.org/10.1080/07328319208021702
Abstract
Reaction of 02,3′-anhydro-5′-0-trityl-2′-deoxycytidine (1) with LiN3s in DMF resulted in the formation of 1-(3-azido-2,3-dideoxy-5-0-trityl-β-D-erythro-pentofuranosyl) cytosine (2) and 3-0-(4-amino-1,3-pyrimidin-2-yl)-5-0-trityl-2-deoxy-α-D-threo-pentofuranosyl azide (3) (2:3 = 1:1) in 88% yield. Compound 3 was deprotected with 80% aqueous AcOH yielding 4Keywords
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