Nucleobase protection with allyloxycarbonyl.
This unit describes protocols for preparation of N-allyloxycarbonyl-protected 5'-O-(4,4'-dimethoxytrityl)-2'-deoxyribonucleosides and 2'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)ribonucleosides. These provide useful building blocks not only for synthesis of natural oligonucleotides but also for artificial analogs with chemically sensitive (particularly, base-labile) modified nucleoside bases or internucleotide linkages. These protected nucleosides are stable to conditions used for conversion to the corresponding nucleoside phosphoramidites and subsequent oligonucleotide synthesis, and the N-allyloxycarbonyl protecting group can be easily and cleanly removed by an organopalladium-catalyzed reaction under mild, nearly neutral conditions.
Hyodo
Mamoru
M
Nagoya University, Nagoya, Japan.
Hayakawa
Yoshihiro
Y
D002384:Catalysis; D002855:Chromatography, Thin Layer; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009841:Oligonucleotides / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet
D007659:Ketones; D009841:Oligonucleotides; D010165:Palladium