Format

Send to

Choose Destination
See comment in PubMed Commons below
Curr Protoc Nucleic Acid Chem. 2007 Mar;Chapter 14:Unit 14.5. doi: 10.1002/0471142700.nc1405s28.

Synthesis of 2'- and 3'-C-methylribonucleosides.

Author information

1
InterMune, Brisbane, California, USA.

Abstract

A simple, efficient method for the synthesis of 2'- and 3'-C-methylribonucleosides starting from a common precursor is described. This synthesis achieves conversion of 1,2:5,6-di-O-isopropylidene-3-C-methyl-alpha-D-allofuranose into 1,2,3-tri-O-acetyl-5-O-benzoyl-3-C-methyl-alpha,beta-D-ribofuranose followed by condensation with nucleic acid bases, with a final ammonolysis leading to 3'-C-methylribonucleosides. Alternatively, the same branched allofuranose converted to l,2,3-tri-O-acetyl-5-O-p-methylbenzoyl-2-C-methyl-beta-D-ribofuranose, after analogous Vorbruggen condensation and ammonolysis, provides 2'-C-methylribonucleosides.

PMID:
18428970
DOI:
10.1002/0471142700.nc1405s28
[Indexed for MEDLINE]
PubMed Commons home

PubMed Commons

0 comments
How to join PubMed Commons

    Supplemental Content

    Full text links

    Icon for Wiley
    Loading ...
    Support Center