2'-C-branched ribonucleosides. 2. Synthesis of 2'-C-beta-trifluoromethyl pyrimidine ribonucleosides

N S Li; X Q Tang; J A Piccirilli

doi:10.1021/ol0155687

2'-C-branched ribonucleosides. 2. Synthesis of 2'-C-beta-trifluoromethyl pyrimidine ribonucleosides

Org Lett. 2001 Apr 5;3(7):1025-8. doi: 10.1021/ol0155687.

Authors

N S Li¹, X Q Tang, J A Piccirilli

Affiliation

¹ Howard Hughes Medical Institute, Department of Biochemistry and Molecular Biology, The University of Chicago, 5841 S. Maryland Avenue, MC 1028, Chicago, Illinois 60637, USA.

PMID: 11277786
DOI: 10.1021/ol0155687

Abstract

[structure: see text]. The first synthesis of 2'-C-beta-trifluoromethyl pyrimidine ribonucleosides is described. 1,2,3,5-Tetra-O-benzoyl-2-C-beta-trifluoromethyl-alpha-D-ribofuranose (3) is prepared from 1,3,5-tri-O-benzoyl-alpha-D-ribofuranose (1) in three steps and converted to 3,5-di-O-benzoyl-2-C-beta-trifluoromethyl-alpha-D-1-ribofuranosyl bromide (5). The 1-bromo derivative (5) is found to be a powerful reaction intermediate for the synthesis of ribonucleosides. The reaction of silylated pyrimidines with (5) in the presence of HgO/HgBr2 affords exclusively the beta-anomers (6-8). Deprotection of (6-8) with ammonia in methanol yields the 2'-C-beta-trifluoromethyl nucleosides (9-11).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Glycosylation
Molecular Conformation
Molecular Structure
Pyrimidines / chemical synthesis*
Pyrimidines / chemistry
Ribonucleosides / chemical synthesis*
Ribonucleosides / chemistry

Substances

Pyrimidines
Ribonucleosides