Tetrabutylammonium Fluoride → HCID 69083734, compound

Participants

Reaction Steps

(3aR,5R,6S,7R,7aR)-6,7-bis(4-methoxybenzyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-N,N-dimethyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-amine (9.5 g, 15.8 mmol) in THF (100 mL) was treated with TBAF (8.27 g, 31.6 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 1-2.5% MeOH in dichloromethane to give compound 10 as a yellow oil (7.0 g, 86%). (ES, m/z): [M+H]+ 489.0; 1H NMR (300 MHz, CDCl3) δ 7.32-7.62 (m, 2H), 7.22-7.28 (m, 2H), 6.85-6.91 (m, 4H), 6.26-6.28 (d, J=6.6 Hz, 1H), 4.52-4.73 (m, 4H), 4.31-4.34 (d, J=11.4 Hz, 1H), 4.23 (s, 1H), 181 (s, 6H), 3.53-3.76 (m, 4H), 3.01 (m, 6H), 1.78-1.82 (m, 1H).

Provenance & Evidence