Nucleotide,XVIII. Synthese und Eigenschaften von (tert-Butyldimethylsilyl)guanosinen,Guanosin-3′-phosphotriestern und Guanosin-haltigen Oligoncleotiden

Nucleotides, XVIII. Synthesis and Properties of (tert-Butyldimethylsilyl)guanosines, Guanosine-3′-Phosphotriesters and Guanosine-containing Oligonucleotides Silylation of N²-benzoyl- (1) and N²-isobutyrylguanosin (2) by tert-butyldimethylsilyl chloride led to the various mono-, di- and tri-O-tert-butyldimethylsilyl derivatives 3–15 . The synthesis of 2′- (24–31) and 3′-phosphotriesters ( 16–23 and 32 ) could be achieved by phosphorylations of partially protected guanosines. The guanosine-3′-phosphodiester 33 and the 5′-OH-guanosine-3′-phosphotriester 34 are used in condensation reactions as 5′- and 3′-terminal components, respectively, to form dinucleoside mono- ( 39 and 40 ) and diphosphates (41–48) in relatively good yields. The various products were characterized by elemental analyses, ¹H-, ¹³C-, and ³¹P-NMR spectra as well as UV and CD spectra.