3′-Selective modification of a 4′,5′-didehydro-5′-deoxy-2′,3′-epoxyuridine using nucleophiles

Highly functionalized 1‐exo‐alkylidene‐2,3‐anhydro‐, and 1′‐halo‐1‐exo‐alkylidene‐2,3‐anhydrofuranoses can be prepared in four or five steps, respectively, from D‐mannose. These compounds feature a variety of functionalities, including a double bond, an oxirane, an allylic oxirane and (in the case of the 1′‐halo derivative) an alkenyl halide. The reactivity of each functionality in these derivatives has been explored, and the usefulness of these substrates has been demonstrated with the preparation of furanose‐based carbohydrate templates with up to four sites of molecular diversity.

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1‐exo‐Alkylidene‐2,3‐anhydrofuranoses: Valuable Synthons in the Preparation of Furanose‐Based Templates

Gómez

Pedregosa

Uriel

et al. 2010

Eur J Org Chem

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One‐pot synthesis of novel 2′‐deoxyuridine derivatives containing α‐aminophosphonate moieties

Shang

Chen

Huang

2007

Heteroatom Chemistry

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A series of α‐aminophosphonate derivatives of 2′‐deoxyuridine (8a–k) have been prepared from 5′‐O‐tert‐butyldimethylsilyl‐3′‐amino‐2′, 3′‐dideoxyuridine in good yields. The structures of all the products were confirmed by 1H NMR, 31P NMR, 31C NMR, and IR spectroscopy, and mass spectrometry and elemental analyses. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:230–235, 2007; Published online in Wiley InterScience (http://www.interscience.wiley.com). DOI 10.1002/hc.20288

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Rearrangement of allylic azide and phenylthio groups of 3′-azido- or 3′-phenylthio-4′,5′-didehydro-5′-deoxyarabinofuranosyluridines

et al. 2005

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3′-Selective modification of a 4′,5′-didehydro-5′-deoxy-2′,3′-epoxyuridine using nucleophiles

Cited by 3 publications

References 47 publications

1‐exo‐Alkylidene‐2,3‐anhydrofuranoses: Valuable Synthons in the Preparation of Furanose‐Based Templates

1‐exo‐Alkylidene‐2,3‐anhydrofuranoses: Valuable Synthons in the Preparation of Furanose‐Based Templates

One‐pot synthesis of novel 2′‐deoxyuridine derivatives containing α‐aminophosphonate moieties

Rearrangement of allylic azide and phenylthio groups of 3′-azido- or 3′-phenylthio-4′,5′-didehydro-5′-deoxyarabinofuranosyluridines

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