Sodium Cyanide → HCID 136395938, compound

Participants

Reaction Steps

8-bromo-2'-deoxyguanosine is reacted with sodium cyanide in DMF. The resulting 8-position modified nucleoside is then reduced with Pd-hydrogen to give 8-aminomethyl-2'- deoxyguanosine. This compound is then condensed with N-Fmoc-aminocaproic acid-pentafluorophenyl ester. This introduces a --CH2 --NH--CO--(CH2)5 --NH-Fmoc functionality at the 8-position of guanosine. Further treatment with (CH3)3SiCl, isobutyric anhydride and NH4OH yielded N2 -isobutyryl protected 8-position functionalized guanosine. Treatment with dimethoxytrityl chloride and pyridine added a DMT blocking group at the 5'-position. Finally phosphitylation gave the desired phosphoramidite compound which is incorporated into oligonucleotides.

Provenance & Evidence