The Journal of Organic Chemistry

A regiocontrolled synthesis of N7-and N9-guanine nucleosides

P Garner, S Ramakanth

Index: Garner, Philip; Ramakanth, Sarabu Journal of Organic Chemistry, 1988 , vol. 53, # 6 p. 1294 - 1298

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Citation Number: 87

Abstract

The reaction of 2-0-acetylated and 2-0-benzoylated glycosides 3a, b/4a, b with silylated p- acetylguanine 7 selectively gave"'-guanine nucleosides 8a, b/Sa, b under kinetically controlled conditions (SnC14/CH3CN, room temperature), whereas 2-0-benzoylated glycosides 3b/4b selectively gave the isomeric Ns-guanine nucleosides lob/1 lb under thermodynamically controlled conditions (TMSOTf/(CH, Cl),, reflux). Unambiguous ...