tert-butyl ((3S,7S,8R,9S)-7-benzyl-9-methyl-2-oxo-8-(((E)-3-oxobut-1-en-1-yl)oxy)-1,5-dioxonan-3-yl)carbamate → HCID 86701246, compound

Participants

Reaction Steps

To a solution of tert-butyl ((3S,7S,8R,9S)-7-benzyl-9-methyl-2-oxo-8-(((E)-3-oxobut-1-en-1-yl)oxy)-1,5-dioxonan-3-yl)carbamate (601 mg, 1.34 mmol, 1.00 equiv) in EtOAc (13 mL) was added 10% Pd/C (72 mg, 0.067 mmol, 0.050 equiv). The resulting suspension was stirred under an atmosphere of hydrogen (1 atm, balloon) overnight. The catalyst was then filtered through a pad of Celite® that was flushed with EtOAc. The filtrate was concentrated to provide an oil. Purification by automated silica gel column chromatography (10-50% EtOAc in hexanes) provided tert-butyl ((3S,7S,8R,9S)-7-benzyl-9-methyl-2-oxo-8-(3-oxobutoxy)-1,5-dioxonan-3-yl)carbamate (417 mg, 69%) as well as tert-butyl ((3S,7S,8R,9S)-7-benzyl-8-(3-hydroxybutoxy)-9-methyl-2-oxo-1,5-dioxonan-3-yl)carbamate (86 mg, 14%).

Provenance & Evidence