Boron Trichloride → HCID 71152431, compound

Participants

Reaction Steps

The protected material, tert-butyl ((3aR,5S,6S,7aR)-6-(benzyloxy)-5-((S)-1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate (0.105 g, 0.214 mmol), was deprotected using BCl3, as described for Example 20. After purification on silica gel by flash column chromatography (1.0 M NH3 in MeOH/DCM, 1:12), (3aR,5S,6S,7aR)-2-(methylamino)-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 (0.051 g, 79%). 1H NMR (400 MHz, CD3OD) δ 6.18 (d, J=6.8 Hz, 1H), 4.46-4.42 (m, 1H), 4.20-4.17 (m, 1H), 3.53 (d, J=7.2 Hz, 1H), 2.85 (s, 3H), 2.32-2.27 (m, 1H), 2.09-2.02 (m, 1H), 1.33 (s, 3H); 13C NMR (100 MHz, CD3OD) δ 164.34, 127.46 (q, J=285.3 Hz), 91.10, 77.04, 75.83 (q, J=26.9 Hz), 70.56, 66.52, 33.66, 30.94, 18.67 (q, J=2.2 Hz); MS, (ES, m/z) [M+H]+ 301.1.

Provenance & Evidence