Reaction Steps
The above material, tert-butyl ((3aR,5S,6R,7R,7aR)-6-(benzyloxy)-7-fluoro-5-((R)-1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(ethyl)carbamate (0.100 g, 0.191 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-((R)-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 (0.053 g, 84%). 1H NMR (400 MHz, CD3OD) δ 6.26 (d, J=6.8 Hz, 1H), 5.04-4.92 (m, 1H), 4.54-4.50 (m, 1H), 4.15-4.07 (m, 1H), 3.73 (d, J=8.6 Hz, 1H), 3.34-3.21 (m, 2H), 1.33 (s, 3H), 1.17 (t, J=7.2 Hz, 3H); 13C NMR (100 MHz, CD3OD) δ 163.47 (d, J=2.2 Hz), 127.40 (q, J=284.2 Hz), 93.11 (d, J=175.6 Hz), 89.36, 75.75 (q, J=27.3 Hz), 73.50 (d, J=27.2 Hz), 72.90, 68.94 (d, J=25.7 Hz), 39.95, 16.72 (q, J=1.5 Hz), 14.98; MS, (ES, m/z) [M+H]+ 333.1.
