Synthesis of 6‐amino‐6‐ 14 C‐hexyl 1‐thio‐α‐D‐mannopyranoside

Abstract The radiolabeled insulin‐like carbohydrate derivative, 6‐amino‐6‐ 14 C‐hexyl 1‐thio‐α‐D‐mannopyranoside ( 6 ), has been synthesized for receptor binding and mechanism‐of‐action studies by a two‐step process from 5‐bromopentyl 1‐thio‐α‐D‐mannopyranoside (4). Nucleophilic displacement reaction on compound 4 with sodium cyanide‐ 14 C and subsequent catalytic reduction of the intermediate nitrile 5 afforded after chromatography the radiochemically pure amine 6 with a specific activity of 47·3 mCi/mmol.