title: Nucleobase protection with allyloxycarbonyl.
abstract: 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.
authors.affiliation: Nagoya University, Nagoya, Japan.
authors.forename: Mamoru
authors.initials: M
authors.lastname: Hyodo
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Hayakawa
mesh_terms: 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
chemical_list: D007659:Ketones; D009841:Oligonucleotides; D010165:Palladium