Efficient synthesis of 2'-deoxynucleoside 3'-C-phosphonates: reactivity of geminal hydroxyphosphonate moiety.
In this report we present a novel, simple way for the synthesis of 3'-C-phosphonate derivatives of all four basic 2'-deoxynucleosides in both fully protected and deprotected forms. The reactivity of the geminal hydroxy phosphonate moiety located at the 3'-carbon atom of the nucleoside was studied with respect to the use of this type of nucleoside phosphonic acid for the preparation of short oligonucleotides, namely, dinucleoside monophosphate analogues.
Králíková
S
S
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague, Czech Republic.
Budĕsínský
M
M
Masojidková
M
M
Rosenberg
I
I
D004247:DNA / Q000138:chemical synthesis*; D003853:Deoxyribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry*; D013053:Spectrophotometry
D003853:Deoxyribonucleosides; D063065:Organophosphonates; D004247:DNA