[(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[(4-bromophenyl)methyl]-4-methyl-indolin-1-yl]tetrahydropyran-2-yl]methyl acetate → 3-(4-bromophenylmethyl)-4-methyl-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indole

Participants

Reaction Steps

Add manganese (IV) oxide (172.5 mmol) to a solution of [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[(4-bromophenyl)methyl]-4-methyl-indolin-1-yl]tetrahydropyran-2-yl]methyl acetate (5.85 mmol) in dichloromethane (20 mL). Stir at room temperature for 48 hours. Filter the reaction through diatomaceous earth and concentrate under reduced pressure. Treat the crude product with dichloromethane/methanol (30 mL of 10:1) and stir for 15 minutes. Filter the resulting precipitate and rinse the filter cake with methanol (2×10 mL). Dry the filter cake under vacuum to yield the title compound as a colorless solid (2.5 g 3.97 mmol): MS (m/z): 630 (M+H).

Provenance & Evidence