Tetrahedron Letters p. 6857 - 6860 (1997)
Update date:2022-08-04
Topics:
Kamaike, Kazuo
Takahashi, Hiroaki
Kakinuma, Takashi
Morohoshi, Kimio
Ishido, Yoshiharu
A novel 2-(levulinyloxymethyl)-5-nitrobenzoyl (LMNBz) protecting group for the 5' position of nucleoside 3'-phosphoramidites was successfully applied to the solid-phase synthesis of both an oligodeoxyribonucleotide (TpTpT and TpTpTpT) and an octaribonucleotide in combination with a 2'-O-Thp protecting group (UpCpApGpUpUpGpG). The LMNBz group was simply unmasked due to its base-labile property by a two-step procedure, i.e., treatments with 0.5 M hydrazine hydrate in 1:4 acetic acid - pyridine, and then with 0.5 M imidazole in acetonitrile.
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