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17044378609
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note
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[5a]
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18
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0033544402
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During the course of our synthetic studies on nucleoside antibiotics, it was revealed that the introduction of a protecting group or substituent on this type of alcohol was quite difficult: S. Ichikawa, S. Shuto, M. Matsuda, J. Am. Chem. Soc. 1999, 121, 10270-10280.
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19
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0025790925
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A similar concept was reported in N-glycosidation to synthesize nucleoside derivatives: T. Kusumi, T. Fukushima, I. Ohtani, H. Kakisawa, Tetrahedron Lett. 1991, 32, 2939-2942.
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0025790925
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The stereochemistry of the 5′ position of 5 was determined to be the R configuration by the modified Mosher method with the amide derivatives, which were prepared by deprotection of the Cbz protecting group of 5 and subsequent acylation of the liberated amine with 2-methoxy-2- trifluoromethylphenylacetic acid (see the Supporting Information); T. Kusumi, T. Fukushima, I. Ohtani, H. Kakisawa, Tetrahedron Lett. 1991, 32, 2939-2942.
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17044405521
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note
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Details for the preparation and characterization may be found in the Supporting Information.
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25
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17044401011
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note
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1H NMR spectrum.
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29
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17044375930
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note
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3, N,N-dimethylformamide).
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17044397334
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note
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It was presumed that the methyl source was the formaldehyde generated upon cleavage of the BOM protecting group from the 3 position.
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33
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