- Chemical synthesis of 5’-β-glycoconjugates of vitamin B6
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Various 5’-β-saccharides of pyridoxine, namely the mannoside, galactoside, arabinoside, maltoside, cellobioside and glucuronide, were synthesized chemically according to KOENIGS-KNORR conditions using α4,3-O-isopropylidene pyridoxine and the respective acetobromo glycosyl donors with AgOTf (3.0 eq.) and NIS (3.0 eq.) as promoters at 0 °C. Furthermore, 5’-β-[13C6]-labeled pyridoxine glucoside (PNG) was prepared starting from [13C6]-glucose and pyridoxine. Additionally, two strategies were examined for the synthesis of 5’-β-pyridoxal glucoside (PLG).
- Bachmann, Thomas,Schnurr, Christian,Zainer, Laura,Rychlik, Michael
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supporting information
(2020/02/15)
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- Synthesis of beta-L-2'-deoxy nucleosides
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An improved process for the preparation of 2′-modified nucleosides and 2′-deoxy-nucleosides, such as, β-L-2′-deoxy-thymidine (LdT), is provided. In particular, the improved process is directed to the synthesis of a 2′-deoxynucleoside that may utilize different starting materials but that proceeds via a chloro-sugar intermediate or via a 2,2′-anhydro-1-furanosyl-nucleobase intermediate. Where an 2,2′-anhydro-1-furanosyl base intermediate is utilized, a reducing agent, such as Red-Al, and a sequestering agent, such as 15-crown-5 ether, that cause an intramolecular displacement reaction and formation of the desired nucleoside product in good yields are employed. An alternative process of the present invention utilizes a 2,2′-anhydro-1-furanosyl base intermediate without a sequestering agent to afford 2′-deoxynucleosides in good yields. The compounds made according to the present invention may be used as intermediates in the preparation of other nucleoside analogues, or may be used directly as antiviral and/or antineoplastic agents.
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Page/Page column 21
(2010/02/11)
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- Design and synthesis of DNA-intercalating 9-fluoren-β-O-glycosides as potential IFN-inducers, and antiviral and cytostatic agents
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Novel 9-fluoren-β-O-glycosides, designed as DNA-intercalating agents in structural correlation with antiviral tilorone and anticancer anthracyclines, have been prepared with yields in β-anomers ranging between 25 and 63%. They have been screened for antiproliferative, immunostimulating and antiviral properties against HSV-1 and HSV-2 viruses. Compounds displaying significant antiviral activity against HSV-2 are acetylated 1 and deprotected 6 9-fluorenyl-O-D-arabinopyranoses, whereas 9-fluorenyl-O-D-glucopyranose 3 is the most effective on HSV-1 replication, followed by 1 and 6. The conformational properties of these compounds have been evaluated by molecular modelling techniques.
- Alcaro,Arena,Neri,Ottana,Ortuso,Pavone,Vigorita
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p. 1781 - 1791
(2007/10/03)
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- New synthesis of L-FMAU from L-arabinose
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A new synthesis of 2′-deoxy-2′-fluoro-5-methyl-β-L-arabinofuranosyl uracil (13, L-FMAU) was achieved in 10 steps from L-arabinose.
- Sznaidman, Marcos L.,Almond, Merrick R.,Pesyan, Amir
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p. 155 - 163
(2007/10/03)
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- Exchange radioiodination produces inversion at C-4 of 1-(4-deoxy-4-iodo-β-D-xylopyranosyl)-2-nitroimidazole
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The title compound, 3a, when exchange labeled with 125I results in three new labeled products. The major labeled product (84.1%) is 1-(4-deoxy-4-iodo-β-L-arabinopyranosyl)-2-nitroimidazole, 3b, that could result from inversion of configuration at C-4. Exchange labeling carried out under conditions of kinetic control yielded dramatically different product ratios than thermodynamic equilibrium reactions. Confirmation of these results was established by extensive 1H NMR spectral analyses. A possible mechanism is presented. Copyright
- Schneider,Price,Chapman
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p. 665 - 673
(2007/10/03)
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