A Reverse Strategy for synthesis of nucleosides based on n-pentenyl orthoester donors

Chem Commun (Camb). 2013 Apr 21;49(31):3251-3. doi: 10.1039/c3cc41036f. Epub 2013 Mar 13.

Abstract

Strategically derivatized NPOE glycosyl donors, are able to efficiently glycosylate silylated nucleobases under mild conditions, even as low as -78 °C if necessary. Ensuring trans-1,2 glycosylation, thus permitting, unlike classical procedures, a Reverse Strategy for the synthesis of ribonucleosides, where glycosylation occurs late, rather than early, and convergency is optimized.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Esters
  • Glycosylation
  • Ribonucleosides / chemistry*
  • Silicon / chemistry
  • Stereoisomerism
  • Temperature

Substances

  • Esters
  • Ribonucleosides
  • Silicon