An efficient synthesis of y-nucleoside (wyosine) by regiospecific methylation of n 4-desmethylwyosine using organozinc reagent

H Bazin, XX Zhou, C Glemarec, J Chattopadhyaya

Index: Bazin, H.; Zhou, X-X.; Glemarec, C.; Chattopadhyaya, J. Tetrahedron Letters, 1987 , vol. 28, # 28 p. 3275 - 3278

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Citation Number: 37

Abstract

The reaction of the organozinc reagent, produced by the reaction of CH 2 I 2 + Zn(C 2 H 5 ) 2 + glyme in diethylether at 20 °C, regioselectively methylates the N 4 -nitrogen of N 4 -desmethylwyosine-triacetate to give pure wyosine-triacetate in 76% isolated yield; no trace of the isomeric N 5 methylated product is found in the latter reaction. Synthesis of a new congener of Y-nucleoside is also reported for the first time from compound in a high overall yield ...