Synthetic utility of an isolable nucleoside phosphonium salt.
The reaction of O6-benzyl-3',5'-bis- O-( tert-butyldimethylsilyl)-2'-deoxyxanthosine with 1H-benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) yielded the nucleoside C-2 tris(dimethylamino)phosphonium hexafluorophosphate salt as a stable, isolable species. This is in contrast to reactions of inosine nucleosides with BOP, where the in situ formed phosphonium salts undergo subsequent reaction to yield O6-(benzotriazol-1-yl)inosine derivatives. The phosphonium salt obtained from the 2'-deoxyxanthosine derivative can be effectively used to synthesize N2-modified 2'-deoxyguanosine analogues. Using this salt, a new synthesis of an acrolein-2'-deoxyguanosine adduct has also been accomplished.
Bae
Suyeal
S
Department of Chemistry, The City College and The City University of New York, New York, New York 10031-9198, USA.
Lakshman
Mahesh K
MK
D003853:Deoxyribonucleosides / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification*
D003853:Deoxyribonucleosides; D009943:Organophosphorus Compounds; C530365:nucleoside C-2 tris(dimethylamino)phosphonium hexafluorophosphate salt