Facile preparation of the oxetane-nucleosides

Org Biomol Chem. 2005 Dec 21;3(24):4362-72. doi: 10.1039/b511406c. Epub 2005 Nov 7.

Abstract

Efficient and practical large scale synthesis of suitably protected 1',2'-oxetane locked purine and pyrimidine nucleosides for incorporation in oligo-DNA or -RNA by solid-phase synthesis is reported. A high regio and stereoselectivity with preferential formation of the beta-anomer in the glycosylation reaction, using the Vorbrüggen procedure, was achieved by a convergent synthetic procedure with orthogonal protection strategy using either 1,2-di-O-acetyl-3,4-O-isopropylidene-6-O-(4-toluoyl)-d-psicofuranose or 2-O-acetyl-6-O-benzyl-1,3,4-tri-O-(4-toluoyl)-d-psicofuranose as the glycosyl donor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrates / chemistry
  • Ethers, Cyclic / chemistry*
  • Molecular Structure
  • Nucleosides / chemistry*

Substances

  • Carbohydrates
  • Ethers, Cyclic
  • Nucleosides
  • oxetane