Helvetica chimica acta

A direct synthesis of nucleoside analogs homologated at the 3'-and 5'-positions

J Schmidt, B Eschgfaller, SA Benner

Index: Schmidt, Juergen; Eschgfaeller, Bernd; Benner, Steven A. Helvetica Chimica Acta, 2003 , vol. 86, # 9 p. 2937 - 2958

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Citation Number: 8

Abstract

A new route is presented to prepare analogs of nucleosides homologated at the 3'-and 5'- positions. This route, applicable to both the d-and l-enantiomeric forms, is suitable for the preparation of monomeric bishomonucleosides needed for the synthesis of oligonucleotide analogs. It begins with the known monobenzyl ether 3 of pent-2-yne-1, 5-diol, which is reduced to alkenol 4. Sharpless asymmetric epoxidation of 4, followed by opening of the ...