Synthesis of 2', 3'-differentiated ribonucleosides via glycosylation reactions with 2-O-Me or 2-O-TBDMS ribofuranose derivatives. 1. Pyrimidine series

…, RH Wightman, JC Ziegler, JL Imbach

Index: Chavis, C.; Dumont, F.; Wightman, R. H.; Ziegler, J. C.; Imbach, J. L. Journal of Organic Chemistry, 1982 , vol. 47, # 2 p. 202 - 206

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Citation Number: 43

Abstract

Discussion The required 2-substituted sugars 2 and 3 were prepared from the readily available 1, 3, 5-tri-O-benzoyl-a-~-ribo-furanose (1) 18 (Scheme I). Reaction of 1 with diazomethane in the presence of BF3 etherate to prevent acyl migration21 produced 2 (-75 9%) always accompanied by some starting material 1 (-15%). Varying reaction conditions could never achieve complete conversion of the starting sugars.

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