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References
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Spectroscopic data for cis-5 and cis-6 were given as follows: (2S)(5R)(6R)-2,5-cis-5: 1H NMR (δ, ppm): 0.81–0.97 (m, 611, -CH3), 1.22–1.63 (m, 15H, -CH,-), 1.76–2.26 (m, 5H, other methylene and methine protons), 3.46 (dt, J = 8.9, 6.7 Hz, 111, ring proton), 3.60–3.78 (m, 2H, ring methylene), 4.01 (t, J = 6.6 Hz, 2H, -0 CH,-), 4.29 (ddd, J = 5.6, 9.2, 18.7 Hz, 1H, ring proton), 6.37–6.44 (m, 1H, ring proton), 6.99(d, J = 8.8 Hz, 2H, aromatic protons) 7.58 (d, J = 8.8 Hz, 2H, aromatic protons), 7.64 (d, J = 8.4 Hz, 2H, aromatic protons), 8.08 (d, J = 8.4 Hz, 2H, aromatic protons); 19F NMR (S, ppm) (internal CFC13 in CDC13):-129.07 (dd, J = 18.7, 278.4 Hz, 1F), -119.21 (dd, J = 5.6, 278.4 Hz, 1F), -82.28 (s, 3F). (2R)(5R)(6R)-2,5-trans-5: 1H NMR: 0.84–0.98 (m, 611, CH3). 1.25–1.65 (m, 14H,-CH,-), 1.73–1.95 (m, 4H, other methylene), 2.11–2.42 (m, 2H, other protons), 3.45 (dt, J = 8.9, 6.6 Hz, 1H, ring proton),3.58(dt,J = 8,9, 6.5 Hz, 1H, ring proton), 3.68–3.79 (m, 1H, ring proton), 4.01 (t, J = 6.6 Hz, 2H,-OCH2-), 4.14 (ddd, J=6.7, 6.7, 20.1 Hz. 1H, ring proton), 6.13 (dd, J = 2.6, 6.6 Hz, 1H, ring proton). 6.98 (d, J = 8.8 Hz, 2H, aromatic protons), 7.55 (d, J = 8.8 Hz, 2H, aromatic protons), 7.62 (d, J = 8.4 Hz, 2H, aromatic protons), 8.09 (d, J = 8.4 Hz, 2H, aromatic protons); 19F NMR:-128.52 (dd, J = 20.1, 277.5 Hz, 1F), -120.15 (dd, J = 7.0, 277.5 Hz, 1F), -82.36 (s, 3F). (2R)(5R)(6R)-2,5-cis-6: 1H NMR: 0.79–1.02 (m, 6H, CH3), 1.22–1.70 (m, 15H,-CH2-), 1.76–2.28 (m, 5H, -CH2- and -CH-), 3.45 (dt, J = 9.6, 6.5 Hz, 114, -O-CH2-), 3.72 (dt, J = 9.6, 6.7 Hz, 1H, -O-CH2-), 4.00 (t, J = 6.5 Hz, 2H, -OCH2-), 4.46 (ddd, J = 4.8, 9.5, 18.9 Hz, 111, ring proton), 4.88–4.93 (m, IH, ring proton), 5.30–5.42 (m, 1H, ring proton), 6.98 (d, J = 8.6 Hz, 2H, aromatic protons), 7.55 (d, J = 8.7 Hz, 2H, aromatic protons), 7.62 (d, J = 8.3 Hz, 2H, aromatic protons), 8.06 (d, J = 8.3 Hz, 2H, aromatic protons); 19F NMR: -128.98 (dd, J = 19.0, 280.0 Hz, 1F),-119.44 (dd, J = 4.8, 280.0 Hz, 1F), -82.17 (s, 3F); Mass (m/e): M+ calcd. for C32H41F5O5 600.2874, obsd. 600.2854; IR (cm−1): 1725, 1610, 1500, 1270, 1190. (2S)(5R)(6R)-2,5trans-6: 0.82–1.01 (m, 6H, CH3-), 1.21–2.07 (m, 19H,-CHZ-), 2.43–2.54 (m, 9H, -CH-), 3.46 (dt, J = 9.4, 6.7 Hz, 1H, -O-CH2-), 3.85 (dt, J = 9.4, 6.6 Hz, 1H,-O-CH2-), 4.01 (t, J = 6.5 Hz, 2H, -O-CH2-), 4.19 (ddd, J = 5.0, 9.4, 18.1 Hz, 1H, ring proton), 4.61 (dd, J = 2.0, 8.7 Hz, 1H, ring proton), 5.28-–.40 (m, 1H, ring proton), 6.98 (d, J = 8.7 Hz, 2H, aromatic protons), 7.55 (d, J = 8.7 Hz, 2H, aromatic protons), 7.62 (d, J = 8.3 Hz, 2H, aromatic protons), 8.04 (d, J = 8.3 Hz, 2H, aromatic protons); 19F NMR: -129.26 (dd, J = 18.1, 279.6 Hz, 1F),-119.55 (dd, J = 5.0, 279.6 Hz, 1F), -82.31 (s, 3F); Mass: M+ calcd. for C32H41F5O5 600.2874, obsd. 600.2889; IR: 1720, 1610, 1505, 1280, 1200.
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Itoh, K., Takeda, M., Namekawa, M. et al. Pentafluoroethylated pyranose derivatives as the chiral dopant for ferroelectric liquid crystals. J Mater Sci Lett 14, 1002–1003 (1995). https://doi.org/10.1007/BF00274631
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DOI: https://doi.org/10.1007/BF00274631