Facile synthesis of monoacetylated spermidines, illustrating selective deacetylation and application of a common precursor

Acta Chem Scand (Cph). 1989 Nov;43(10):990-4. doi: 10.3891/acta.chem.scand.43-0990.

Abstract

The synthesis of all three monoacetylated spermidines is reported. N4-Acetylspermidine was obtained in four steps from spermidine via the triacetylated intermediate by selective deacetylation after exhaustive t-butoxycarbonylation as well as directly from a previously described protected precursor. N1-Acetylspermidine and N8-acetylspermidine were both obtained in four simple protection/deprotection steps from a common, selectively protected compound, thus illustrating the versatility of the latter.

MeSH terms

  • Dealkylation
  • Indicators and Reagents
  • Spermidine / analogs & derivatives
  • Spermidine / chemical synthesis*
  • Spermidine / chemistry

Substances

  • Indicators and Reagents
  • N(8)-acetylspermidine
  • N(1)-acetylspermidine
  • N(4)-acetylspermidine
  • N(1)-benzyloxycarbonyl-N(8)-butoxycarbonylspermidine
  • Spermidine