HCID 86751606, compound → HCID 86751605, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (2S,3R,4E)-2-Azido-3-benzoyloxy-1-(2,3-di-O-benzoyl-4,6-di-O-tert-butyloxycarbonylmethyl-α-D-galactopyranosyloxy)-4-octadecene described in Example 1-F (0.145 g, 0.14 mmol) in aqueous trifluoroacetic acid (90%, 3 mL) was stirred at 22° C. during 5 minutes. The solvents were evaporated under vacuum and the residue was co-evaporated with toluene (3×5 mL) and then dissolved in a mixture of dioxane/water (1:1, 10 mL). This mixture was stirred at 22° C. for 30 minutes. The solvents were evaporated under vacuum and the residue was co-evaporated again with toluene (4×10 mL). The residue was purified by silica gel plates (chloroform/methanol/water 75:25:2). The residue upon solvent evaporation was redissolved in methylene chloride/methanol (1:1, 40 mL) and treated at 0° C. (ice bath) with Dowex 50W X8 (H+) resin for 40 minutes to give the title compound (0.076 g, 59%).

Provenance & Evidence