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)(methyl)carbamate (0.200 g, 0.394 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, 1:15), (3aR,5S,6R,7R,7aR)-7-fluoro-2-(methylamino)-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 (0.114 g, 91%). 1H NMR (400 MHz, CD3OD) δ 6.29 (d, J=6.8 Hz, 1H), 5.05-4.93 (m, 1H), 4.55-4.51 (m, 1H), 4.15-4.08 (m, 1H), 3.73 (d, J=8.6 Hz, 1H), 2.85 (s, 3H), 1.34 (s, 3H); 13C NMR (100 MHz, CD3OD) δ 164.35 (d, J=2.7 Hz), 127.35 (q, J=284.3 Hz), 93.14 (d, J=175.8 Hz), 89.65, 75.73 (q, J=27.3 Hz), 73.40 (d, J=27.2 Hz), 72.90, 68.88 (d, J=25.6 Hz), 30.85, 16.75 (q, J=1.3 Hz); MS, (ES, m/z) [M+H]+ 318.1.
