A NEW METHOD FOR SYNTHESIZING THE ANTINEOPLASTIC NUCLEOSIDES 1-(2-AZIDO-2-DEOXY-β-D-ARABINOFURANOSYL)CYTOSINE (CYTARAZID) AND 1-(2-AMINO-2-DEOXY-β-D-ARABINOFURANOSYL)CYTOSINE (CYTARAMIN) FROM URIDINE

Akira MATSUDA; Johji YASUOKA; Tohru UEDA

doi:10.1248/cpb.37.1659

Akira MATSUDA, Johji YASUOKA, Tohru UEDA

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Keywords: cytarazid, cytaramin, uridine, N3-benzoyluridine, diethyl azo-dicarboxylate, diphenylphosphorazide, intermolecular nucleophilic substitution, 1-(2-azido-2-deoxy-β-D-arabinofuranosyl)cytosine, 1-(2-amino-2-deoxy-β-D-arabinofuranosyl)cytosine

JOURNAL FREE ACCESS

1989 Volume 37 Issue 6 Pages 1659-1661

DOI https://doi.org/10.1248/cpb.37.1659

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Abstract

A new method was developed for synthesizing of antineoplastic nucleosides 1-(2-azido-2-deoxy-β-D-arabinofuranosyl)cytosine (2) and 1-(2-amino-2-deoxy-β-D-arabinofuranosyl)-cytosine (3) from uridine. The reaction of N3-benzoyluridine derivative (5) with DPPA, triphenylphosphine and diethyl azodicarboxylate gave the desired 2'-azido-arabinosyl derivative (6), which was subsequently transformed to lead 2 and 3.

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