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Transprotection in solid phase peptide synthesis: Easy conversion of Fmoc carbamates into Boc carbamates

✍ Scribed by Ricardo L.E. Furlán; Ernesto G. Mata


Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
130 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis


A one-pot conversion of N-fluorenylmethoxycarbonyl (Fmoc) amino acids and dipeptides linked to Wang resin into the corresponding N-tert-butoxycarbonyl (Boc) derivatives was achieved in very high yields. The transformation was corroborated by cleaving of the Boc derivatives with trimethyltin hydroxide.


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Direct conversion of Fmoc-protected amin
✍ Florencio Zaragoza; Henrik Stephensen 📂 Article 📅 2000 🏛 Elsevier Science 🌐 French ⚖ 95 KB

Support-bound, Fmoc-protected amines react with aliphatic alcohols in the presence of ADDP, PBu 3 , and DIPEA to yield O-alkyl carbamates. The reaction presumably proceeds via O-alkylation of an intermediate carbamate anion.