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Diazotization of S‑Sulfonyl-cysteines

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Figshare2019-10-28 更新2026-04-29 收录
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https://figshare.com/articles/dataset/Diazotization_of_i_S_i_Sulfonyl-cysteines/10059821
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We report the preparation of enantiomerically enriched β-thio-α-hydroxy and α-chloro carboxylic acid and ester building blocks by diazotization of S-sulfonyl-cysteines. The thiosulfonate protecting group demonstrated resistance to oxidation and attenuation of sulfur’s nucleophilicity by the anomeric effect. The key transformation was optimized by a 22 factorial design of experiment, highlighting the unique reactivity of cysteine derivatives in comparison with aliphatic amino acids.
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2019-10-28
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