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1H NMR was very straightforward: the secondary hydroxyl group of the desired isomer 5 appeared as a doublet at 2.30 ppm, while the primary alcohol proton of the thermodynamic isomer 6 appeared as a doublet of doublets at 2.34 ppm. In addition, the observed 13C NMR chemical shift values for the isopropylidene acetal- and methyl carbons correlated well with the general chemical shift regions reported for five-membered acetonides: Buchanan, J. G.; Chacón-Fuertes, M. E.; Edgar, A. R.; Moorhouse, S. J.; Rawson, D. I.; Wightman, R. H. Tetrahedron Lett. 1980, 21, 1793-1796. Buchanan, J. G.; Edgar, A. R.; Rawson, D. I.; Shahidi, P.; Wightman, R. H. Carbohydr. Res. 1982, 100, 75-86.
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1H NMR was very straightforward: the secondary hydroxyl group of the desired isomer 5 appeared as a doublet at 2.30 ppm, while the primary alcohol proton of the thermodynamic isomer 6 appeared as a doublet of doublets at 2.34 ppm. In addition, the observed 13C NMR chemical shift values for the isopropylidene acetal- and methyl carbons correlated well with the general chemical shift regions reported for five-membered acetonides: Buchanan, J. G.; Chacón-Fuertes, M. E.; Edgar, A. R.; Moorhouse, S. J.; Rawson, D. I.; Wightman, R. H. Tetrahedron Lett. 1980, 21, 1793-1796. Buchanan, J. G.; Edgar, A. R.; Rawson, D. I.; Shahidi, P.; Wightman, R. H. Carbohydr. Res. 1982, 100, 75-86.
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The protection of arabitol as its bis-pentylidene acetal has been communicated very recently: Maleczka, R. E., Jr.; Terrell, L. R.; Geng, F.; Ward, J. S., III Org. Lett. 2002, 4, 2841-2844.
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Wiley: New York; Chapters 3 and 5
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Permutation of two ligands of the double bond does not lead to a stereoisomer. For a clear discussion about stereogenicity/chirotopicity, see: (a) Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; Chapters 3 and 5, pp 53 and 123.
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Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, Germany, Chapter 1
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(b) Helmchen, G. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, Germany, 1995: Vol. E21a, Chapter 1, pp 17-21.
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Helmchen, G.1
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0242665986
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note
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Both a single carbon and an olefinic double bond (axis) can be stereogenic elements. See ref 19a, pp 52-53 and 1208, and ref 19b, pp 11-13.
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84
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0242665985
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note
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2-symmetric if it did not contain a central chirotopic, nonstereogenic double bond (axis).
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85
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0242582018
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note
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2-symmetric compounds" (refs 9 and 24).
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33748639758
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Kim, J. H.; Yang, M. S.; Lee, W. S.; Park, K. H J. Chem. Soc., Perkin Trans. 1 1998, 2877-2880.
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85004762419
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Napolitano, E.; Fiaschi, R.; Mastrorilli, E. Synthesis 1986, 122-125. The preparation was slightly modified: CSA was used instead of p-TsOH, and 5 equiv of methanol was used instead of 15 equiv. We found that it was important to purify the 3,3-dimethoxypentane by fractional distillation (bp 125 °C, atmospheric pressure) before use in the protection reaction.
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Synthesis
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The United Kingdom Database Service. Fletcher, D. A.; McMeeking, R. F.; Parkin, D. J. Chem. Inf. Comput. Sci. 1996, 36, 746.
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