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First synthesis of 2′-oxabicyclo[3.1.0]hexyl nucleosides with a north conformation |
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| Authors: | Won Hee Kim Jin-Ah Kang Jin-Ah Kim Pusoon Chun Chong-Kyo Lee Hyung Ryong Moon |
| Institution: | a Laboratory of Medicinal Chemistry, College of Pharmacy and Research Institute for Drug Development, Pusan National University, 30 Jangjeon-dong, Geumjeong-gu, Busan 609-735, Republic of Korea b Department of Chemistry, The University of Suwon, Kyunggi 445-743, Republic of Korea c Pharmacology Research Center, Korea Research Institute of Chemical Technology, Daejon 305-600, Republic of Korea d Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120-750, Republic of Korea |
| Abstract: | The first synthesis of 2′-oxabicyclo3.1.0]hexyl nucleosides, a novel class of bicyclonucleosides, with a north conformation was successfully accomplished starting from (S)-epichlorohydrin via a tandem alkylation-lactonization, a less steric hindrance-dependent silylation in equilibrium and a coupling reaction with nucleobases under Vorbruggen conditions. Addition of acetic acid prevented a benzoyl group from migrating during desilylation with TBAF. 1H NMR and X-ray crystallographic analysis indicated that the anomeric effect worked on the β-2′-oxabicyclo3.1.0]hexyl nucleosides. |
| Keywords: | Oxabicyclo[3 1 0]hexyl nucleosides North conformation Anomeric effect X-ray structure |
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