A “clickable” vitamin B12 derivative possessing the azide functionality at the 5′-position was synthesized by means of a two-step procedure on the gram scale. The reaction of cobalamin with mesyl chloride (MsCl) afforded the 5′-OMs derivative, which was subsequently transformed to the desired 5′-azide, the structure of which was confirmed using X-ray analysis. It proved to be reactive in the azide–alkyne 1,3-dipolar cycloaddition reaction to give substituted triazoles in high yields. A study of the reaction conditions and the scope of the process are reported.
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