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