(Acyloxy)alkoxy moiety as amino acids protecting group for the synthesis of (R,R)-2,7 diaminosuberic acid via RCM

Protein Pept Lett. 2012 Dec;19(12):1245-9. doi: 10.2174/092986612803521666.

Abstract

A new synthetic pathway is described to prepare asymmetrically protected 2,7-diaminosuberic acid. This strategy exploits (acyloxy)alkoxy promoiety as protecting group and RCM reaction using second generation Grubbs catalyst and provides the trans isomer of (2R,7R)-7-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-(tert-butoxycarbonylamino)-8- methoxy-8-oxooct-4-enoic acid, which was in turn reduced to obtain (2R,7R)-7-(((9H-fluoren-9-yl)methoxy)carbonylamino)- 2-(tert-butoxycarbonylamino)-8-methoxy-8-oxooctanoic acid.

MeSH terms

  • Alcohols / chemistry*
  • Amino Acids / chemistry*
  • Chemical Phenomena
  • Diaminopimelic Acid / analogs & derivatives*
  • Diaminopimelic Acid / chemical synthesis
  • Diaminopimelic Acid / chemistry
  • Models, Molecular
  • Spectrometry, Mass, Electrospray Ionization
  • Stereoisomerism

Substances

  • 2,7-diaminosuberic acid
  • Alcohols
  • Amino Acids
  • alkoxyl radical
  • Diaminopimelic Acid