Synlett 1994; 1994(10): 853-855
DOI: 10.1055/s-1994-23030
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The Synthesis of 1′-Methyl Carbocyclic Thymidine and its Effect on Nucleic Acid Duplex Stability

Karl-Heinz Altmann* , Rudolf Kesselring
  • *CIBA, Central Research Laboratories, R-1060.2.34, CH-4002 Basel, Switzerland.
Further Information

Publication History

Publication Date:
22 March 2002 (online)

The enantioselective synthesis of the title compound 1 has been accomplished in 18 chemical steps starting from cyclopentadiene via epoxide 2 and amine 9 as the central key intermediates. Oligodeoxyribonucleotides incorporating several modified building blocks 1 are still capable of hybridizing to complementary RNA, albeit with lower affinity than their natural counterparts.