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Syntheses of 5′‐deoxy‐5‐[ 18 F] fluorouridine and related compounds as probes for measuring tissue proliferation in vivo
Author(s) -
Shiue ChyngYann,
Wolf Alfred P.,
Friedkin Morris
Publication year - 1984
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580210910
Subject(s) - chemistry , sodium methoxide , methanol , acetic acid , hydrolysis , in vivo , radiochemistry , deoxyuridine , chemical synthesis , stereochemistry , organic chemistry , in vitro , biochemistry , dna , microbiology and biotechnology , biology
A rapid synthesis of 5′‐deoxy‐5‐[ 18 F] fluorouridine ( 3a ) from either [ 18 F] F 2 or CH 3 CO 2 18 F is described. Fluorination of 2′,3′‐di‐ O ‐acetyl‐5′‐deoxyuridine ( 1a ) with either [ 18 F] F 2 or CH 3 CO 2 18 F in glacial acetic acid at room temperature followed by hydrolysis with sodium methoxide in methanol gives 5′‐deoxy‐5‐[ 18 F] fluorouridine ( 3a ) in radiochemical yields of 20‐25% in a synthesis time of 80 min from EOB. The same method also has been used to synthesize 5‐[ 18 F] fluorouridine ( 3b ) and 2′‐deoxy‐5‐[ 18 F] fluorouridine ( 3c ) in similar radiochemical yields. Acetyl hypofluorite (CH 3 CO 2 F) is proposed as an intermediate for these reactions.