4-Nitrobenzoyl chloride → 2,3,4-Tri-o-benzyl-1-o-p-nitrobenzoyl-alpha-l-fucopyranose

Participants

Reaction Steps

Since both the α and β isomers yielded the same β-bromide (compound 9), it was decided to skip the column purification and instead use the mixture as such. In this case, 2,3,4-tri-O-benzyl-L-fucopyranose (compound 6) (25 g, 55 mmol) was treated with p-nitrobenzoyl chloride (compound 7) as described above and the crude material (33.0 g) was dissolved in CH2Cl2 (100 mL) and simply filtered through a short column of silica gel. This removed the color and other polar material. This procedure furnished the anomeric mixture of esters (compound 8) as a gummy material (25.7 g, yield 80%).

Provenance & Evidence