Enantioselective desymmetrization of FTY720

Chem Pharm Bull (Tokyo). 2014;62(10):1041-4. doi: 10.1248/cpb.c14-00462.

Abstract

A method for enantioselective desymmetrization of N-Ac and N-Boc-FTY720 by nonenzymatic asymmetric acylation was developed. Effective enantioselective monobenzoylation using benzoyl chloride in the presence of the tetraphenylbisoxazoline (L2)-CuCl2 complex gave the desired products 3a and 3b in 52-62% yield with 64% ee.

MeSH terms

  • Acylation
  • Benzoates / chemistry
  • Catalysis
  • Coordination Complexes / chemistry
  • Copper / chemistry
  • Fingolimod Hydrochloride
  • Oxazoles / chemistry
  • Propylene Glycols / chemistry*
  • Solvents / chemistry
  • Sphingosine / analogs & derivatives*
  • Sphingosine / chemistry
  • Stereoisomerism

Substances

  • Benzoates
  • Coordination Complexes
  • Oxazoles
  • Propylene Glycols
  • Solvents
  • Copper
  • Fingolimod Hydrochloride
  • Sphingosine
  • cupric chloride
  • benzoyl chloride