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약학대학
약학과
Journal papers
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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
SCOPUS Author ID
정낙신
Issue Date
2010
Journal Title
Tetrahedron
ISSN
0040-4020
Citation
Tetrahedron vol. 66, no. 9, pp. 1706 - 1715
Indexed
SCI; SCIE; SCOPUS
Document Type
Article
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
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