Tetrahedron

SnCl 4 versus TiCl 4-mediated coupling between N-6-benzoyladenine and perbenzoylated 2-deoxypyranose: Application to the synthesis of certain homochiral acyclo …

MV Baud, C Chavis, M Lucas, JL Imbach

Index: Baud, Marie-V.; Chavis, Claude; Lucas, Marc; Imbach, Jean-L. Tetrahedron, 1991 , vol. 47, # 48 p. 9993 - 10002

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Citation Number: 15

Abstract

1, 3, 4-tri-0-benzoyl 2-deoxyribopyranose and persilylated N-6-benzoyladenine react in two different and regioselective ways according to the nature of the coupling reagent SnCl4 or TiCl4. The former Lewis acid gives rise to the anomeric mixture of N-9 nucleosides and the latter affords mainly 3′-deoxy 3′-(N-6-benzoyl-9-adenyl) glycals. These two series of derivatives constitute useful synthons for the preparation of homochiral acyclo and ...