Tin tetrachloride → 4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)-2,3,6-tri-O-acetyl-beta-D-glucopyranosyl azide

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Reaction Steps

A mixture of β-lactose octaacetate (203 mg, 0.3 mmol), trimethylsilyl azide (41 mg, 0.35 mmol), and SnCl4 (40 mg, 0.15 mmol) in CH2Cl2 (1.5 ml) was stirred overnight at room temperature. The solution was diluted with CH2Cl2 (20 ml) and washed twice with 1 M potassium fluoride solution (5 ml), water (5 ml) and evaporated affording 4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide (25) (178 mg 90%).

Provenance & Evidence