Tetrabutylammonium Fluoride → HCID 69280755, compound

Participants

Reaction Steps

To a solution of tert-butyl (5R,6S,7R)-6,7-bis(4-methoxybenzyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(propyl)carbamate (19 g, 26.50 mmol) in tetrahydrofuran (100 mL) was treated with TBAF (13.8 g, 53 mmol) overnight at room temperature. The resulting solution was diluted with brine (200 mL), extracted with ethyl acetate (2×200 mL), and dried over anhydrous magnesium sulfate. After removal of solvents, the residue was purified by silica gel column, eluted with 10-30% ethyl acetate in petroleum ether to give compound 19 as a yellow oil (14.5 g, 91%). (ES, m/z): [M+H]+ 603.0; 1H NMR (300 MHz, CDCl3) 7.32-7.35 (d, J=8.7 Hz, 2H), 7.17-7.20 (d, J=8.7 Hz, 2H), 6.83-6.92 (m. 4H), 6.04-6.06 (d, J=6.9 Hz, 1H), 4.64-4.66 (m, 2H), 4.40-4.48 (m, 1H), 4.17-4.38 (m, 3H), 3.72-3.83 (m, 9H), 3.45-3.60 (m, 2H), 3.43-3.45 (m, 1H), 1.58-1.63 (m, 2H), 1.53 (s, 9H), 0.78-0.83 (t, J=7.2 Hz, 3H).

Provenance & Evidence