4‐Fluorophenyl 3‐nitro‐2‐pyridinesulfenate as a practical protecting agent for amino acids |
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| Authors: | Yan Cui Cédric Rentier Akihiro Taguchi Kentaro Takayama Atsuhiko Taniguchi Yoshio Hayashi |
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| Institution: | Department of Medicinal Chemistry, Tokyo University of Pharmacy and Life Sciences, Hachioji, Tokyo, Japan |
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| Abstract: | We report a new protecting agent ( 1 , Npys‐OPh(pF)) for 3‐nitro‐2‐pyridine (Npy) sulfenylation of amino, hydroxy, and thiol functional groups. Several Npys phenoxides were synthesized from Npys chloride (Npys‐Cl) and phenols in the presence of base in 1‐step reaction, and their ability for Npy‐sulfenylation was evaluated. As a result, 1 was selected as a new Npy‐sulfenylation agent with advantages including improved physicochemical stability, more controllable reactivity, and easier handling than the conventional protecting agent Npys‐Cl. |
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| Keywords: | 3‐nitro‐2‐pyridinesulfenyl (Npys) group amino acid Npys phenoxides protecting agent stability sulfenylation |
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