HCID 90177793, compound → HCID 90177037, compound

Participants

Reaction Steps

(2S,3S,4R,5S,6R)-2-(3-(4-((E)-4-methoxy-4-oxobut-1-en-1-yl)benzyl)-4-methylphenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (8, 1.74 g, 3.0 mmol) was dissolved in a 1:1 (v:v) THF/MeOH solution. Pd/C (10% wet, 174 mg) was added and the reaction hydrogenated at 40 psi for 3 hours. The reaction was monitored by 1H NMR. Upon completion, the reaction was filtered over Celite with excess MeOH. Removal of solvents in vacuo provided the product as a light yellow solid (1.65 g, 94% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.11-7.20 (m, 2 H), 7.07 (t, J=7.8 Hz, 3 H), 6.99 (d, J=8.1 Hz, 2 H), 5.33 (dd, J=9.6 Hz, 1 H), 5.21 (dd, J=9.6 Hz, 1 H), 5.12 (dd, J=9.6 Hz, 1 H), 4.52 (d, J=9.9 Hz, 1 H), 4.39 (d, J=9.9 Hz, 1 H), 3.85-4.00 (m, 2 H), 3.67 (s, 3 H), 2.61 (t, J=7.6 Hz, 2H), 2.33 (t, J=7.5 Hz, 2 H), 2.21 (s, 3 H), 2.18 (s, 3 H), 2.10 (s, 3 H), 2.01 (s, 3 H), 1.93 (quin, J=7.6 Hz, 2 H), 1.75 (s, 3 H). MS (ES+) [M+NH4]+=604.

Provenance & Evidence