Reaction Steps
The above material, tert-butyl ((3aR,5S,6R,7R,7aR)-6-(benzyloxy)-7-fluoro-5-((S)-1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(ethyl)carbamate (0.057 g, 0.11 mmol), was deprotected with BCl3 using the procedure described for Example 20. After purification on silica gel by flash column chromatography (1.0 M NH3 in MeOH/DCM, 1:17), (3aR,5S,6R,7R,7aR)-2-(ethylamino)-7-fluoro-5-((S)-1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-6-ol was obtained as a white solid (0.031 g, 85%). 1H NMR (400 MHz, CD3OD) δ 6.30 (d, J=6.8 Hz, 1H), 5.03-4.90 (m, 1H), 4.54-4.49 (m, 1H), 4.20-4.13 (m, 1H), 3.61 (d, J=8.5 Hz, 1H), 3.30-3.22 (m, 2H), 1.36 (s, 3H), 1.17 (t, J=7.2 Hz, 3H); 13C NMR (100 MHz, CD3OD) δ 163.48 (d, J=1.7 Hz), 127.48 (q, J=285.5 Hz), 93.70 (d, J=177.4 Hz), 88.94, 75.79 (q, J=27.0 Hz), 74.76 (d, J=1.4 Hz), 73.79 (d, J=26.7 Hz), 68.15 (d, J=25.1 Hz), 40.02, 18.92 (q, J=2.2 Hz), 14.95; MS, (ES, m/z) [M+H]+ 333.1.
