Stereospecific fluorination of 1,3,5-tri-O-benzoyl-alpha-D-ribofuranose-2-sulfonate esters: preparation of a versatile intermediate for synthesis of 2 '-[F-18]-fluoro-arabinonucleosides

Authors
Alauddin, MM Conti, PS Mathew, T Fissekis, JD Prakash, GKS Watanabe, KA
Citation
Mm. Alauddin et al., Stereospecific fluorination of 1,3,5-tri-O-benzoyl-alpha-D-ribofuranose-2-sulfonate esters: preparation of a versatile intermediate for synthesis of 2 '-[F-18]-fluoro-arabinonucleosides, J FLUORINE, 106(1), 2000, pp. 87-91
Citations number
20
Categorie Soggetti
Inorganic & Nuclear Chemistry
Journal title
JOURNAL OF FLUORINE CHEMISTRY
ISSN journal
00221139 → ACNP
Volume
106
Issue
1
Year of publication
2000
Pages
87 - 91
Database
ISI
SICI code
0022-1139(200010)106:1<87:SFO1>2.0.ZU;2-L
Abstract
A detailed investigation on fluorination of 1,3,5-tri-O-benzoyl-alpha -D-ri bofuranose-2-sulphonate esters is reported. Various combinations of sulfona te esters, fluorinating agents and solvents were evaluated in this study. O rganic ammonium fluoride, in particular n-Bu4NF, was found to be better flu orinating agent than inorganic fluoride, and 1,3,5-tri-O-benzoyl-alpha -D-r ibofuranose-2-trifluoramethylsulphonate ester appeared to be the best subst rate. The developed method is suitable for stereospecific (arabino) incorpo ration of radiofluorine (F-18) into the sugar moiety. (C) 2000 Elsevier Sci ence S.A. All rights reserved.