Concepedia

<i>p</i>-Methoxybenzyl as a New <i>N</i>3-Imide Protecting Group of 5-Fluorouridine and Its Application to the Synthesis of 5′-<i>O</i>-Acryloyl-5-fluorouridine

Takahiko Akiyama, Masahiro Kumegawa, Yasuhiro Takesue, Hiroyuki Nishimoto, Shoichiro Ozaki

Chemistry Letters · 1990 · 17 citations · 9 references

DOI

Concepts

Abstract

Abstract 5′-O-Acryloyl-5-fluorouridine was prepared by use of p-methoxybenzyl(PMB) group as a new N3-imide protecting group of 5-fluorouridine. A chemoselective method for protection has been developed by use of ethyldiisopropylamine as a base and deprotection was effected by AlCl3-anisole system.

References

9

Synthetic studies on β-lactam antibiotics. VII. Mild removal of the benzyl ester protecting group with aluminum trichloride

Teruji Tsuji, Takahiro Kataoka, M. YOSHIOKA et al. · Tetrahedron Letters · 1979 · 93 citations

, , +8

The protection of uracil and guanine residues in oligonucleotide synthesis

Simon S. Jones, Colin B. Reese, Samson Sibanda et al. · Tetrahedron Letters · 1981 · 72 citations

, , +14

General method for the preparation of N3- and O4-substituted uridine derivatives by phase-transfer reactions

Mitsuo Sekine · The Journal of Organic Chemistry · 1989 · 64 citations

, , +4

Methoxyethoxymethyl group for the protection of uracil residue in oligoribonucleotide synthesis

Hiroshi Takaku, Souichi Ueda, Tsunehiko Ito · Tetrahedron Letters · 1983 · 45 citations

, , +9

A NEW PROTECTING TACTICS FOR THE URACIL RESIDUE IN OLIGORIBONUCLEOTIDE SYNTHESIS

Takashi Kamimura, Tsukio Masegi, K. URAKAMI et al. · Chemistry Letters · 1983 · 35 citations

, , +8