Azidotrimethylsilane → HCID 178476366, compound

Participants

Reaction Steps

3,4,6-tri-O-Acetyl-2-deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-ethylamino]-α-D-glucopyranosyl bromide (3) (60 g, 0.112 mol) is suspended in acetonitrile (280 mL) and trimethylsilylazide (TMS-N3) (29.9 mL, 0.224 mol) is added dropwise followed by the dropwise addition of tetrabutylammonium fluoride (1 M TBAF in tetrahydrofuran) (225 mL, 0.225 mol). The reaction is stirred for 16 hr protected from light. The solvents are removed under reduced pressure, and the residue is preabsorbed on silica (150 g) and the product eluted with ethyl acetate/petroleum ether (1:1) (2 L). The solvents are evaporated and the crude residue used directly in the next step.

Provenance & Evidence