Towards the synthesis of 2'-fluorinated pyrimidine-based nucleosides

College

College of Science

Department/Unit

Chemistry

Document Type

Article

Source Title

Asia Life Sciences

Volume

25

Issue

1

First Page

445

Last Page

452

Publication Date

2016

Abstract

The progress towards the development of a model system for late-stage fluorination of pyrimidine-based nucleosides is described in this paper. The synthesis involved the introduction of a cyclic protecting group on the 3' - and 5' -hydroxyls of a ribose sugar that locks its conformation and reorients the nucleobase away from blocking an incoming nucleophile. Subsequent use of electron withdrawing protecting groups in the pyrimidine nucleobase modulated the nucleophilicity of C-2 carbonyl group oxygen to prevent its neighboring group participation. Specifically, the use of triazole protecting group in the pyrimidine nucleobase afforded greater versatility by allowing easy access to either the uridine and cytidine analogs depending on the deprotection condition that will be used.

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Disciplines

Chemistry

Keywords

Pyrimidine nucleotides; Triazoles; Uridine; Cytidine diphosphate choline

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