Stereospecific deuteration of alpha-furanosyl azomycin nucleosides : a model reaction for tritium radiolabeling
Stereospecific synthesis of 1-alpha-d-(2-deuteroribofuranosyl)-2-nitroimidazole (2'-[(2)H]-alpha-AZR) is reported. This, deuteration was independent of the configuration of C-2' -OH group (arabinose or ribose) in sugar moiety of starting molecules. Slightly better yield (>37%) of the deuterated product, 6, from arabinosyl precursor in comparison to corresponding ribose precursor (29%) was obtained which may reflect better stereochemical availability of C-2' -OH in arabinose during oxidation.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2008 |
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| Erschienen: |
2008 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:18 |
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| Enthalten in: |
Bioorganic & medicinal chemistry letters - 18(2008), 11 vom: 01. Juni, Seite 3256-60 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Kumar, Piyush [VerfasserIn] |
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| Links: |
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| Themen: |
10028-17-8 |
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| Anmerkungen: |
Date Completed 09.07.2008 Date Revised 19.11.2015 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1016/j.bmcl.2008.04.055 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM179569163 |
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| 245 | 1 | 0 | |a Stereospecific deuteration of alpha-furanosyl azomycin nucleosides |b a model reaction for tritium radiolabeling |
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| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Stereospecific synthesis of 1-alpha-d-(2-deuteroribofuranosyl)-2-nitroimidazole (2'-[(2)H]-alpha-AZR) is reported. This, deuteration was independent of the configuration of C-2' -OH group (arabinose or ribose) in sugar moiety of starting molecules. Slightly better yield (>37%) of the deuterated product, 6, from arabinosyl precursor in comparison to corresponding ribose precursor (29%) was obtained which may reflect better stereochemical availability of C-2' -OH in arabinose during oxidation | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 7 | |a Nitroimidazoles |2 NLM | |
| 650 | 7 | |a Nucleosides |2 NLM | |
| 650 | 7 | |a Tritium |2 NLM | |
| 650 | 7 | |a 10028-17-8 |2 NLM | |
| 650 | 7 | |a azomycin |2 NLM | |
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| 700 | 1 | |a Emami, Saeed |e verfasserin |4 aut | |
| 700 | 1 | |a McEwan, Alexander J B |e verfasserin |4 aut | |
| 700 | 1 | |a Wiebe, Leonard I |e verfasserin |4 aut | |
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