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17844362961
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77955304689
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note
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The configuration of the newly forming stereocenter (C4) of 7 was confirmed by NMR analysis of a single diastereomeric 5-hydroxy-4-{2-(4- methoxyphenoxy)propyl}-2-phenyl-1,3-dioxane obtained through a process including conventional hydrogenation of 7, separation of epimers at C6, hydrolysis of the acetonide, and benzylidene acetal formation.
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34
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77955305159
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note
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5 The reduced coordination ability of the α-oxygen of ent-6 due to steric hindrance may interfere with the Z-enolate formation to result in the low ratio of ent-4 to 17 in polar solvents. However, in toluene, the low solvation ability of toluene may destabilize the E-enolate rather than the Z-enolate, stabilized by the cyclic chelate, to enhance the ratio of ent-4.
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37
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77955303533
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The time-dependent increase of the ratio of ent-4 might be attributable to the different lifetimes of E- and Z-enolates
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The time-dependent increase of the ratio of ent-4 might be attributable to the different lifetimes of E- and Z-enolates.
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38
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2142858450
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3 of an alcohol derived from 2 via removal of the THP group. For modified Mosher's method, see: I. Ohtani, T. Kusumi, Y. Kashman, and H. Kakisawa J. Am. Chem. Soc. 113 1991 4092
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77955308555
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note
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+]: 292.1674, found: 292.1668.
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45
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35548987589
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M.J. Robins, I. Nowak, S.F. Wnuk, F. Hansske, and D. Madej J. Org. Chem. 72 2007 8216
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46
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77955303632
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The details will be described elsewhere
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The details will be described elsewhere.
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