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First synthesis of 2′-oxabicyclo[3.1.0]hexyl nucleosides with a north conformation

Title
First synthesis of 2′-oxabicyclo[3.1.0]hexyl nucleosides with a north conformation
Authors
Kim W.H.Park A.-Y.Kang J.-A.Kim J.Kim J.-A.Lee H.-R.Chun P.Choi J.Lee C.-K.Jeong L.S.Moon H.R.
Ewha Authors
정낙신
Issue Date
2010
Journal Title
Tetrahedron
ISSN
0040-4020JCR Link
Citation
vol. 66, no. 9, pp. 1706 - 1715
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
The first synthesis of 2′-oxabicyclo[3.1.0]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′-oxabicyclo[3.1.0]hexyl nucleosides. © 2010 Elsevier Ltd. All rights reserved.
DOI
10.1016/j.tet.2010.01.014
Appears in Collections:
약학대학 > 약학과 > Journal papers
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