Synthesis of 1-O-R-5-deoxy-?-D-ribofuranosides with (CH3)2As and (CH3)2As?O as substituents at the 5-position and a methyl or 2?,3?-dihydroxypropyl group as the aglycone in the 1-position
1996; Wiley; Volume: 10; Issue: 1 Linguagem: Inglês
10.1002/(sici)1099-0739(199602)10
ISSN1099-0739
AutoresJinggao Liu, Daniel H. O'Brien, Kurt J. Irgolic,
Tópico(s)DNA and Nucleic Acid Chemistry
ResumoSix arsenic-containing β-D-ribofuranosides, including the naturally occurring (2′R)-dimethyl[1-O-(2′,3′-dihydroxypropyl)-5-deoxy-β-D-ribofuranos-5-yl]arsine oxide, were prepared in multi-step reactions from D-ribose and tetramethyldiarsine. The synthetic procedure uses the early substitution of the hydroxy group with bromine at C5, subsequent attachment of a chiral three-carbon aglycone at C1, and final delivery of arsenic at C5. The synthesis provides a viable route for the preparation of multigram quantities of the natural product.
Referência(s)