Sodium Acetate → (1R,3R,4S,5S)-3-[(3,3-Dimethyl-1,3-dihydro-isobenzofuran-5-ylmethyl)-amino]-5-[3-fluoro-4-nitro-5-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzyl]-1-oxo-hexahydro-1lambda*4*-thiopyran-4-ol

Participants

Reaction Steps

The title compound was prepared in an analogous manner as described for example 1h, starting from (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 (0.075 g, 0.19 mmol), 3,3-dimethyl-1,3-dihydro-isobenzofuran-5-carbaldehyde (0.036 g, 0.203 mmol), NaOAc (0.032 g, 0.38 mmol) and NaBH3CN (0.013 g, 0.19 mmol) and was obtained as a light yellow foam after chromatographic purification on silica gel: TLC (EtOAc-MeOH 19:1) Rf=0.20; HPLC RtA=1.78 min; ESIMS [M+H]+=575; 1H NMR (400 MHz, CDCl3): δ 7.19 (m, 2H), 7.04 (s, 1H), 6.84 (s, 1H), 6.78 (d, 1H), 5.04 (s, 2H), 4.76 (m, 1H), 4.25 (s broad, 1H), 3.94 (d, 1H), 3.76 (d, 1H), 3.53 (ddd, 1H), 3.37 (ddd, 1H), 2.8-3.15 (m, 5H), 2.14 (m, 2H), 1.52 (d, 3H), 1.48 (s, 6H).

Provenance & Evidence