A carbohydrate-derived trifunctional scaffold for medicinal chemistry library synthesis

Authors

  • Diana I. S. P. Resende University of Aveiro
  • Amalia M. Estévez University of Aveiro
  • Andre M. Alker F. Hoffmann-La Roche
  • Rainer E. Martin F. Hoffmann-La Roche
  • Hans Peter Wessel University of Aveiro

DOI:

https://doi.org/10.13171/mjc72/01809051415-wessel

Abstract

For the generation of compound libraries for drug discovery a central scaffold containing three exit vectors with defined chirality was devised starting from commercially available tri-O-acetyl-glucal. Surprisingly, the reaction of a 4-O-mesylate with sodium azide did not lead to the expected 4-azido-4-deoxy derivative but to a 3-azido-3-deoxy regioisomer via intermediate epoxide formation. The absolute stereochemical configuration of the final tetrahydropyran building block was proven by X-ray crystallography. This scaffold endowed with a carboxylic acid, a secondary alcohol, and an azide functionality may be connected to a DNA tag at any of the three distinct exit vectors, thus providing ready access to several different compound libraries. 

Author Biographies

Diana I. S. P. Resende, University of Aveiro

Department of Chemistry

Amalia M. Estévez, University of Aveiro

Department of Chemistry

Hans Peter Wessel, University of Aveiro

Department of ChemistryInvited Full Professor

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Published

2018-09-05

Issue

Vol. 7 No. 2 (2018)

Section

Medicinal Chemistry

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