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But-2-ynylbisoxycarbonyl Chloride: A Novel $C_2$-Symmetric Reagent for the Protection of Amines and Amino Acids

American Chemical Society
Publication Date
  • Organic Chemistry


A novel $C_2$-symmetric protecting group for amines, the but-2-ynylbisoxycarbonyl (Bbc) group, is developed, which can be deblocked with tetrathiomolybdate under neutral conditions. One equivalent of the bischloroformate, BbcCl, is used for the protection of 2 equiv of the amine. Its application in peptide synthesis is established through the synthesis of a tripeptide, and its orthogonality with Cbz, Fmoc, and Boc groups has been studied.

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