Abstract
The synthesis of a novel compound, 3-deoxy-3-fluoro-β-d-allopyranoside, is described. It involves blocking the 4- and 6-positions of allose to cause fluorination only at the 3-position. This six-step synthesis gave pure crystalline compound in a 5% overall yield. The crystal structure, determined by X-ray diffraction, confirmed the chemical formula and configuration of the product. It showed that the C-F bond isaxial, while the C-(OH) bonds areequatorial. The overall conformation of this fluoroallose is similar to that of allose (Acta Cryst.1984,C40, 1863) (with OH instead of F), but the packing in the two crystals is different in the region of C3, the site of chemical variation.
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Carrell, H. L.; Glusker, J. P.; Burger, V.; Manfre, F.; Tritsch, D.; Biellmann, J.-F.Proc. Natl. Acad. Sci. USA 1989,86, 4440–4444.
Card, P. J.; Reddy, G. S.J. Org. Chem. 1983,48, 4734–4743.
MADNES (Munich Area Detector NE System) Version 1992. J. W. Pflugrath, Cold Spring Harbor Laboratory, and A. Messerschmidt, Max-Planck Institut fuer Biochemie.
Messerschmidt, A.; Pflugrath, J. W.J. Appl. Cryst. 1987,20, 306–315.
Kabsch, W.J. Appl. Cryst. 1988,21, 916–924.
Debaerdemaker, T.; Germain, T.; Main, P.; Refaat, L. S.; Tate, C.; Woolfson, M. M. 1988.MULTAN 88—Computer Programs for the Automatic Solution of Crystal Structures from X-ray Diffraction Data; University of York: York, UK.
Debost, J. L.; Gelas, J.; Horton, D.; Mols, O.Carbo. Res. 1984,125, 329–335.
Pigman, W. W.; Richtmyer, N. K.J. Am. Chem. Soc. 1942,64, 369–374.
Raymond, A. L.; Tipson, R. S.; Levene, P. A.J. Biol. Chem. 1939,130, 47–54; Klemer, A.Chem. Ber. 1959,92, 218–226.
Kroon-Batenburg, L. M. J.; van der Sluis, P.; Kanters, J. A.Acta Cryst. 1984,C40, 1863–1865.
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Myers, C.B., Ramanjulu, M.M., Carrell, H.L. et al. Synthesis and X-ray crystal structure of 3-deoxy-3-fluoro-β-D-allopyranoside. Struct Chem 8, 65–71 (1997). https://doi.org/10.1007/BF02272347
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DOI: https://doi.org/10.1007/BF02272347