Synthesis and conformational properties of 2′??deoxy??2′??methylthio??pyrimidine and??purine nucleosides: Potential antisense applications

…, P Wheeler, P Dan Cook, YS Sanghvi

Index: Fraser; Wheeler; Cook; Sanghvi Journal of Heterocyclic Chemistry, 1993 , vol. 30, # 5 p. 1277 - 1287

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Citation Number: 34

Abstract

Abstract A convenient and shorter synthesis of 2′-deoxy-2′-methylthiouridine analogs 5,− 5-methyluridine 6,-cyti-dine 15,− 5-methylcytidine 16,-adenosine 27 and-guanosine 34 was accomplished. Successful conversion of ribonucleosides (5-methyl U, U, A, G) into the corresponding 2′-substituted nucleosides involves nucleophilic displacement (SN 2) of an appropriate leaving group at the 2′-position by methanethiol, a soft nucleophile. ...