Unit

UNIT 2.4 A Base-Labile Protecting Group (Fluorenylmethoxycarbonyl) for the 5′-Hydroxy Function of Nucleosides

  1. Michael J. Gait1,
  2. Christian Lehmann2

Published Online: 1 MAY 2001

DOI: 10.1002/0471142700.nc0204s00

Current Protocols in Nucleic Acid Chemistry

Current Protocols in Nucleic Acid Chemistry

How to Cite

Gait, M. J. and Lehmann, C. 2001. A Base-Labile Protecting Group (Fluorenylmethoxycarbonyl) for the 5′-Hydroxy Function of Nucleosides. Current Protocols in Nucleic Acid Chemistry. 00:2.4:2.4.1–2.4.22.

Author Information

  1. 1

    MRC Laboratory of Molecular Biology, Cambridge, United Kingdom

  2. 2

    Institute of Organic Chemistry, University of Lausanne, Lausanne, Switzerland

Publication History

  1. Published Online: 1 MAY 2001
  2. Published Print: FEB 2000

Abstract

Many popular synthesis strategies look for appropriate 2′-O-protection methods to use in conjunction with 5′-O-trityl chemistry. In contrast, this unit describes the use of FMOC as a 5′-protecting group in conjunction with a ketal-type 2′-O-protecting group, 4-methoxytetrahydropyran-4-yl (MTHP). The synthesis of all four 2′-O-MTHP-5′-O-FMOC-protected ribonucleosides and 5′-O-FMOC-2′-deoxythymidine is described, as is the preparation of the N-protected, 2′-O-MTHP-protected starting nucleosides.