Unit

UNIT 1.11 Reduction of Ribonucleosides to 2′-Deoxyribonucleosides

  1. Morris J. Robins1,
  2. Stanislaw F. Wnuk2

Published Online: 1 JUL 2005

DOI: 10.1002/0471142700.nc0111s21

Current Protocols in Nucleic Acid Chemistry

Current Protocols in Nucleic Acid Chemistry

How to Cite

Robins, M. J. and Wnuk, S. F. 2005. Reduction of Ribonucleosides to 2′-Deoxyribonucleosides. Current Protocols in Nucleic Acid Chemistry. 21:1.11:1.11.1–1.11.14.

Author Information

  1. 1

    Brigham Young University, Provo, Utah

  2. 2

    Florida International University, Miami, Florida

Publication History

  1. Published Online: 1 JUL 2005
  2. Published Print: JUN 2005

Abstract

Ribonucleosides are converted into 2′-deoxyribonucleosides in good yields by a four-step procedure. Selective protection of the 3′- and 5′-hydroxyl groups with 1,3-dichloro-1,1,3,3-tetraisopropyl-1,3-disiloxane is followed by functionalization of the 2′-hydroxyl group with phenoxythiocarbonyl chloride. Free radical–mediated reductive C2′–O2′ bond cleavage of these 3′,5′-O-TPDS-2′-O-PTC-nucleoside derivatives with tributyltin hydride, followed by removal of the silyl protecting group with tetrabutylammonium fluoride, provides the 2′-deoxyribonucleosides. Adenosine, cytidine, guanosine, and uridine are converted into dA, dC, dG, and dU in overall yields of 60% to 80%. Use of tributyltin deuteride in the reductive cleavage step gives 2′-deuterio-2′-deoxyadenosine in 81% yield from adenosine with >85% retention of configuration at C2′. Application of this four-step protocol with nucleoside analogs is straightforward.

Keywords:

  • 2′-deoxygenation of ribonucleosides;
  • 2′-deoxyribonucleosides;
  • free radical-mediated deoxygenation of ribonucleosides;
  • protection–deprotection at O3′ and O5′ of ribonucleosides