The use of tin(IV) chloride for mild and selective boc deprotection on TFA cleavable Rink-amide MBHA resin

Noam S. Freeman, Chaim Gilon*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

An efficient, straightforward and inexpensive method for selective Boc deprotection on Rink-amide MBHA resin using tin(IV) chloride in dichloromethane is presented. Preliminary results suggest that the low degree of cleavage from the resin accompanying the Boc deprotection may depend on steric hindrance associated with the resin. This method can be useful as a selective deprotection step in solid-phase syntheses of cyclic peptides and small molecules in which only a few Boc deprotection steps are required.

Original languageEnglish
Pages (from-to)2097-2100
Number of pages4
JournalSynlett
Issue number13
DOIs
StatePublished - Aug 2009

Keywords

  • Boc
  • Deprotection
  • Orthogonal protecting groups
  • Rink-amide MBHA resin
  • SPOS
  • SPPS

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