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Cytidine analogues
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and references therein
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(a) McEldoon, W. L.; Wiemer, D. F. Tetrahedron 1995, 51, 7131-7148 and references therein.
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8
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12244272081
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note
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These authors also assigned the major phosphonate derived from phosphite addition to a cytidine aldehyde as the 5′R isomer, although no data for that compound were included in their preliminary report.
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9
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0036020844
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Sendai, Japan, August
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Presented in part at the International Conference on Phosphorus Chemistry, Sendai, Japan, August 2001. Chen, X.; Jung, K.; Wiemer, D. F.; Wiemer, A. J.; Hohl, R. J. Phosphorus, Sulfur, Silicon Relat. Elem. 2002, 177, 1783-1786.
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Presented in part at the International Conference on Phosphorus Chemistry, Sendai, Japan, August 2001. Chen, X.; Jung, K.; Wiemer, D. F.; Wiemer, A. J.; Hohl, R. J. Phosphorus, Sulfur, Silicon Relat. Elem. 2002, 177, 1783-1786.
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(a) Kozlowski, J. K.; Rath, N. P.; Spilling, C. D. Tetrahedron 1995, 51, 6385-6396.
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17
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12244253677
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note
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These assignments also are consistent with the stereochemical outcome of allylation reactions conducted with aldehydes 8 and 18. Reaction of aldehyde 8 with allyltrimethylsilane gave only the 5′R adduct while reaction of aldehyde 18 under the same conditions gave only the 5′S product, as shown by single-crystal diffraction analysis. Furthermore, allylation of aldehyde 23 with allyltrimethylsilane gave only the 5′R adduct, as established by diffraction analysis and also parallel to the course of phosphite addition. Unpublished results from X. Chen and D. F. Wiemer.
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18
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0030561355
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12244264115
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note
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2 from -78 °C to room temperature gave the R adduct as its trimethylsilyl derivative in 64% yield. After hydrolysis of the silyoxy groups, the C-5′ stereochemistry was confirmed by comparison with compound 23a.
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32
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