Nucleosides. Part LV. Efficient synthesis of arabinoguanosine building blocks
1994; Wiley; Volume: 77; Issue: 2 Linguagem: Inglês
10.1002/hlca.19940770203
ISSN1522-2675
AutoresMatthias Resmini, Wolfgang Pfleiderer,
Tópico(s)Polyamine Metabolism and Applications
ResumoAbstract From guanosine ( 1 ) as starting molecule, protected arabinoguanosine derivatives such as phosphoramidite precursors and arabinoguanosine ( 18 ) itself were prepared in high yields. Inversion of the configuration at C(2′) was achieved by introduction of the (trifluoromethyl)sulfonyl residue and subsequent displacement by nucleophiles like acetate, bromide, and azide. The guanine moiety was protected at the amide function by the 2‐(4‐nitrophenyl)ethyl (npe) group on O 6 and at the NH 2 function by the 2‐(4‐nitrophenyl)ethoxycarbonyl (npeoc) group.
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