Diazabicyclo(2.2.2)octane → 1-Propenyl 3-O-benzyl-2-deoxy-2-palmitamido-beta-D-glucopyranoside

Participants

Reaction Steps

To a solution of Compound 5 (3.2 g., 5.84 mmol) in ethanol:benzene:water (7:3:1, v/v) (250 ml.) were added diazabicyclo[2.2.2]octane (0.2 g, 1.8 mmol) and tris(triphenylphosphine) rhodium(I) chloride (0.4 g., 0.43 mmol). The mixture was stirred for 24 h. under reflux. Solvents were evaporated and coevaporated with toluene. A portion of the product, purified on a column of silica gel, afforded an amorphous solid, [α]D25 -7.4°, [α]43625 -13/3° (chloroform).

Provenance & Evidence