{(1R,3R,4S,5S)-5-[3-fluoro-4-nitro-5-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzyl]-4-hydroxy-1-oxo-tetrahydro-thiopyran-3-yl}-carbamic acid tert-butyl ester → (1R,3R,4S,5S)-3-Amino-5-[3-fluoro-4-nitro-5-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzyl]-1-oxo-tetrahydro-thiopyran-4-ol

Participants

Reaction Steps

The title compound was prepared in an analogous manner as described for example 1g, starting from {(1R,3R,4S,5S)-5-[3-fluoro-4-nitro-5-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzyl]-4-hydroxy-1-oxo-tetrahydro-thiopyran-3-yl}-carbamic acid tert-butyl ester and was obtained as a light yellow foam: TLC (CH2Cl2-MeOH-AcOH-H2O 180:20:2:1) Rf=0.10; HPLC RtA=1.50 min; ESIMS [M+H]+=415; 1H NMR (600 MHz, DMSO-d6): δ 8.09 (s, 3H), 7.29 (s, 1H), 7.14 (d, 1H), 6.02 (s broad, 1H), 5.48 (m, 1H), 3.56 (m, 1H), 3.30 (t, 1H), 3.16 (m, 2H), 2.89 (d, 1H), 2.76 (t, 1H), 2.72 (dd, 1H), 2.5-2.6 (m, 2H), 1.46 (d, 3H).

Provenance & Evidence