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Studies on synthesis of phosphate analogues utilizing unprotected H-phosphonates, H-phosphonothioates, and H-phosphonodithioates derived from various natural products are currently under investigation in these laboratories.
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15444358058
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31P NMR and TLC analysis)
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31P NMR and TLC analysis).
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23
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15444354852
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31P NMR and TLC analysis)
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31P NMR and TLC analysis).
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26
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15444355925
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The reaction was carried out on a small scale and the product isolated by paper chromatography
-
The reaction was carried out on a small scale and the product isolated by paper chromatography.
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27
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15444355186
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note
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For example, dithymidine (3′-5′) H-phosphonate (0.25 mmol/2 mL) in the presence of triethylamine (2 equiv) underwent oxidation with sulfur (2 equiv) to the corresponding dinucleoside phosphorothioate within 1 min in DMF or MeOH, ca. 10 min in pyridine, ca. 40 min in dioxane or toluene, and ca. 90 min in carbon disulfide. When triethylamine was replaced by diisopropylamine or DBU, the reaction in dioxane went to completion within 10 and 1 min, respectively (R. Wallin and J. Stawiński, unpublished results).
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29
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0009515999
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31
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15444352882
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31P NMR spectroscopy
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31P NMR spectroscopy.
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32
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15444359728
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31P NMR experiment)
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31P NMR experiment).
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33
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37049083173
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15444352137
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Upon addition of triethylamine to a solution of sulfur in Pyridine, a deep yellow color, characteristic for polysulfides, developed. This disappeared during the course of the reaction with phosphite 11
-
Upon addition of triethylamine to a solution of sulfur in Pyridine, a deep yellow color, characteristic for polysulfides, developed. This disappeared during the course of the reaction with phosphite 11.
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-
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36
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15444341799
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note
-
HP = 659 and 660 Hz) upon further addition of the silylating agent or triethylamine.
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37
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0001426134
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