Unit

Small-Molecule Library Synthesis on Silicon-Functionalized SynPhase Lanterns

  1. Jeremy R. Duvall,
  2. Anita Vrcic,
  3. Lisa A. Marcaurelle

Published Online: 1 JUL 2010

DOI: 10.1002/9780470559277.ch100038

Current Protocols in Chemical Biology

Current Protocols in Chemical Biology

How to Cite

Duvall, J. R., Vrcic, A. and Marcaurelle, L. A. 2010. Small-Molecule Library Synthesis on Silicon-Functionalized SynPhase Lanterns. Current Protocols in Chemical Biology. 2:135–151.

Author Information

  1. Chemical Biology Platform, The Broad Institute of MIT and Harvard, Cambridge, Massachusetts

Publication History

  1. Published Online: 1 JUL 2010
  2. Published Print: JUL 2010

Abstract

Silicon-functionalized SynPhase Lanterns are useful for the combinatorial synthesis of small-molecule libraries. Lanterns bearing an alkyl-tethered diisopropylarylsilane are first activated with triflic acid to afford the corresponding diisopropylsilyl triflate, which is then reacted with a library scaffold bearing a free alcohol. Once the scaffold has been loaded onto the solid phase, a variety of transformations can be run, including amine cappings, cross-coupling reactions, and amide bond formation. These reactions can yield a variety of products when run sequentially using split-pool synthesis strategies. Upon completion of the solid-phase transformations, the small molecules are released from the Lanterns using HF/pyridine. Using the techniques described here, libraries can be made ranging from a few compounds to >10,000 members in a highly efficient manner. Curr. Protoc. Chem. Biol. 2:135-151 © 2010 by John Wiley & Sons, Inc.

Keywords:

  • solid-phase;
  • combinatorial;
  • synthesis;
  • diversity;
  • Lanterns;
  • silicon