A novel method for the synthesis of 4'-thiopyrimidine nucleosides using hypervalent iodine compounds

Naozumi Nishizono; Ryosuke Baba; Chika Nakamura; Kazuaki Oda; Minoru Machida

doi:10.1039/b305644a

A novel method for the synthesis of 4'-thiopyrimidine nucleosides using hypervalent iodine compounds

Org Biomol Chem. 2003 Nov 7;1(21):3692-7. doi: 10.1039/b305644a.

Authors

Naozumi Nishizono¹, Ryosuke Baba, Chika Nakamura, Kazuaki Oda, Minoru Machida

Affiliation

¹ Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan. nishizon@hoku-iryo-u.ac.jp

PMID: 14649900
DOI: 10.1039/b305644a

Abstract

The coupling reactions of cyclic sulfides with a silylated pyrimidine nucleobase using a hypervalent iodine reagent were investigated. The reaction of silylated uracil with cyclic sulfide 12 using PhI=O gave the desired beta-anomer 14 in moderate yield. 4'-Thiouridine (22) was obtained by deprotection of 14.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Iodine / chemistry*
Magnetic Resonance Spectroscopy
Pyrimidine Nucleosides / chemistry*
Spectrometry, Mass, Electrospray Ionization
Thionucleosides / chemical synthesis*

Substances

Pyrimidine Nucleosides
Thionucleosides
Iodine