Synthesis and biological activities of 5-(hydroxymethyl, azidomethyl, or aminomethyl)-2'-deoxyuridine and related 5'-substituted analogs

…, RF Schinazi, MS Chen, WH Prusoff

Index: Shiau, George T.; Schinazi, Raymond F.; Chen, Ming S.; Prusoff, William H. Journal of Medicinal Chemistry, 1980 , vol. 23, # 2 p. 127 - 133

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Citation Number: 55

Abstract

The synthesis of 5-(azidomethyl)-2'-deoxyuridine (10) has been accomplished by two independent methods. The first involved tosylation of 5-(hydroxymethyl)-2'-deoxyuridine (1) to furnish a mixture of two mono-and a ditosyl nucleosides which were converted into the corresponding 5-(azidomethyl)(lo), 5-(azidomethyl)-5'-azido (14), and 5-(hydroxymethyl)-5'- azido (15) derivatives of 2'-deoxyuridine. The second method was more selective and ...