Lipozyme-Mediated Regioselective Esterification of Isosorbide Under Solvent-Free Conditions

References

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• Table 2: GC Retention times (min) of esters of isosorbide. GC analyses were performed on a Fisons Instruments GC 8000 series chromatograph with flame ionization and capillary column OV 1 12m, ID 0.22 mm, ef 0.1 pm, (carrier gas He at 70kPa) with the same gradient for the products a, b, c, d: 100°C to 270°C (10°C/min) then 270°C. For the products e the conditions were: 100°C to 280°C (10°C/min) then 280°C during 35 min. The retention time of isosorbide was 2,43 min. Internal standard for calibration in GC was methyl myristate.
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• 1H NMR spectra were recorded on Brüker 250 MHz spectrometer in CDCl3 with TMS as an internal standard. The optical rotations were measured at 20 °C on P20 Bellingham+Stanley Ltd. Polarimeter. 3a: [α]D=+86.6 (c 1 CH3OH) 1H-NMR (CDCl3): 0.8-0,95 (3H, t, CH3); 1,15-1,42 (8H, m, 4CH2); 1,54-1,73 (2H, m, CH2); 2,27-2,33 (1H, d, OH); 2,33-2,43 (2H, t, CH2); 3,72-3,82 (1H, q, H6a); 3,85-3,97 (3H, m, H1a, 1b, 6b); 4,28-4,37 (1H, broad,H2); 4,37-4,43 (1H, d, H3); 4,81-4,89 (1H, t, H4); 5,1-5,2 (1H, q, H5). 3b: [α]D=+78.2 (c 1 CH3OH) 1H-NMR (CDCl3): 0,8-0,95 (3H, t, CH3); 1,15-1,4 (12H, m, 6CH2); 1,55-1,72 (2H, m, CH2); 2,27-2,34 (1H, broad, OH); 2,32-2,42 (2H, t, CH2); 3,72-3,81 (1H, q, H6a); 3,85-3,96 (3H, m, H1a, 1b, 6b); 4,28-4,37 (1H, broad, H2); 4,37-4,43 (1H, d, H3); 4,82-4,89 (1H, t, H4); 5,1-5,19 (1H, q, H5). 3c: [α]D=+72.6 (c 1 CH3OH), mp=21-22°C 1H-NMR (CDCl3): 0,8-0,93 (3H, t, CH3); 1,15-1,42 (16H, m, 8CH2); 1,55-1,78 (2H, m, CH2); 2,32-2,42 (2H, t, CH2); 3,72-3,82 (1H, q, H6a); 3,85-3,98 (3H, m, H1a, 1b, 6b); 4,3-4,38 (1H, broad, H2); 4,38-4,44 (1H, d, H3); 4,81-4,89 (1H, t, H4); 5,11-5,2 (1H, q, H5). 3d: [α]D=+65.0 (c 1 CH3OH), mp=37-38¶C 1H-NMR (CDCl3): 0,8-1 (3H, t, CH3); 1,15-1,45 (20H, m, 10CH2); 1,5-1,8 (2H, m, CH2); 2,3-2,45 (2H, t, CH2); 3,72-3,82 (1H, q, H6a); 3,87-3,98 (3H, m, H1a, 1b, 6b); 4,3-4,38 (1H, broad, H2); 4,38-4,45 (1H, d, H3); 4,81-4,9 (1H, t, H4); 5,1-5,22 (1H, q, H5). 3e: [α)D=+62.8 (c 1 CH3OH), mp=48.5-49.5°C 1H-NMR (CDCl3): 0,8-0,95 (3H, t, CH3); 1,15-1,45 (24H, m, 12CH2); 1,55-1,75 (2H, m, CH2); 2,3-2,43 (2H, t, CH2); 3,72-3,83 (1H, q, H6a); 3,85-3,98 (3H, m, H1a, 1b, 6b); 4,3-4,38 (1H, broad, H2); 4,38-4,45 (1H, d, H3); 4,82-4,9 (1H, t, H4); 5,12-5,22 (1H, q, H5).
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