Synthesis of 2'-deoxy-2'-fluoroguanyl-(3',5')-guanosine

Tokumi Maruyama; Shigetada Kozai; Kazuo Nakamura; Masachika Irie

doi:10.1081/NCN-120016479

Synthesis of 2'-deoxy-2'-fluoroguanyl-(3',5')-guanosine

Nucleosides Nucleotides Nucleic Acids. 2002 Nov-Dec;21(11-12):765-74. doi: 10.1081/NCN-120016479.

Authors

Tokumi Maruyama¹, Shigetada Kozai, Kazuo Nakamura, Masachika Irie

Affiliation

¹ Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan. maruyama@ph.bunri-u.ac.jp

PMID: 12537019
DOI: 10.1081/NCN-120016479

Abstract

The protected analogue of 2-amnio-6-chloropurine arabinoside (3b) was subjected to reaction with diethylaminosulfur trifluoride (DAST) and subsequently treated with NaOAc in Ac2O/AcOH to give N2, O3', O5'-triacetyl-2'-deoxy-2'-fluoroguanosine (5a). After deacetylation of the sugar moiety and protection of 5'-OH by a 4,4'-dimethoxytrityl group, this nucleoside component was converted to 2'-deoxy-2'-fluoroguanyl-(3',5')-guanosine (6c, GfpG).

MeSH terms

Drug Design
Guanosine / analogs & derivatives*
Guanosine / chemical synthesis*
Guanosine / chemistry
Molecular Structure

Substances

2'-deoxy-2'-fluoroguanyl-(3',5')-guanosine
Guanosine