Fluorine-18 acetyl hypofluorite, produced by a gas/solid-phase reaction, was reacted with D-glucal in water, followed by treatment with HCl and serial passage through columns of charcoal, ion-retardation resin, and alumina. The product was an injectable solution of 2-[18F]fluoro-2-deoxy-D-glucose. The radiochemical purity was greater than 95% and the radiochemical yield was about 40%. The synthesis was completed in about 15 min. Acetyl hypofluorite was shown to be a stable, highly stereoselective fluorinating agent in aqueous systems over a wide pH range.
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J Org Chem
December 2013
School of Chemistry, Tel-Aviv University, Tel-Aviv 69978, Israel.
Aryl boronic acids or pinacol esters containing EDG were converted in good yields and fast reactions to the corresponding aryl fluorides using the readily obtainable solutions of AcOF. In reactions with aryl boronic acids containing EWG at the para position, there are two competing forces: one directing the fluorination to take place ortho to the boronic acid and the other, toward an ipso substitution. With EWG meta to the boronic acid, substitution ipso to the boron moiety takes place in good yields.
View Article and Find Full Text PDFOrg Biomol Chem
March 2012
School of Chemistry, Tel-Aviv University, Tel-Aviv, 69978, Israel.
Activation of the relatively inactive polypyridine backbone with strong electrophilic fluorine, originating from acetyl hypofluorite (AcOF) enables attack of the acetoxy moiety at the α position to the heteroatom. Derivatives of bipyridine, phenanthroline and terpyridine systems have been acetoxylated or oxygenated within a few minutes usually in very good yields.
View Article and Find Full Text PDFJ Org Chem
April 2008
Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia, Canada V6T 1Z1.
The synthesis of a series of 2-deoxy-2,2-dihaloglycosyl halides as potential alpha-glycosidase inactivators has been achieved via the halogenation of protected 2-fluoroglycal precursors. Direct chlorination of per-O-acetylated 2-fluoro-d-glucal and 2-fluoromaltal followed by basic deprotection yielded the corresponding 2-chloro-2-deoxy-2-fluoroglycosyl chlorides. Reaction of the per-O-acetylated 2-fluoroglycals with acetyl hypofluorite or Selectfluor yielded the 2-deoxy-2,2-difluoroglycosyl derivatives, which were converted to their alpha-chlorides using thionyl chloride and deprotected under basic conditions.
View Article and Find Full Text PDFAcc Chem Res
October 2005
School of Chemistry, Tel-Aviv University, Tel-Aviv 69978, Israel.
Elemental fluorine is a starting point for nucleophilic fluorinations (e.g., BrF3), radical fluorinations (e.
View Article and Find Full Text PDFJ Nucl Med
February 2004
Department of Medical Radiation Technology and Institute of Radiological Sciences, National Yang-Ming University, 155 Li-Nong Street, Section 2, Pei-tou, Taipei 112, Taiwan ROC.
Unlabelled: L-p-Boronophenylalanine (BPA) has been applied as a potential boron carrier for the treatment of malignant glioma in clinical boron neutron capture therapy (BNCT) since 1994. To provide the pharmacokinetics of BPA for clinical use of BNCT in Taiwan, 4-borono-2-(18)F-fluoro-L-phenylalanine-fructose ((18)F-FBPA-Fr) was synthesized and the biologic characteristics of this radiotracer in glioma-bearing rats were investigated.
Methods: Radiolabeled (18)F-F(2) was produced via the (20)Ne(d,alpha)(18)F reaction, and (18)F-acetyl hypofluorite ((18)F-AcOF) was generated by passing (18)F-F(2) through a column filled with tightly packed KOAc/HOAc powder.
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