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

被引：24
作者：
Alauddin, MM
Conti, PS
Mathew, T
Fissekis, JD
Prakash, GKS
Watanabe, KA
机构：
[1] Univ So Calif, PET Imaging Sci Ctr, Los Angeles, CA 90033 USA
[2] Univ So Calif, Loker Hydrocarbon Res Inst, Los Angeles, CA 90033 USA
[3] Mem Sloan Kettering Canc Ctr, Organ Chem Lab, New York, NY 10021 USA
来源：
JOURNAL OF FLUORINE CHEMISTRY | 2000年 / 106卷 / 01期
关键词：
fluorination; n-Bu4NF; nucleophilic radiofluorine;
D O I：
10.1016/S0022-1139(00)00307-9
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A detailed investigation on fluorination of 1,3,5-tri-O-benzoyl-alpha -D-ribofuranose-2-sulphonate esters is reported. Various combinations of sulfonate esters, fluorinating agents and solvents were evaluated in this study. Organic ammonium fluoride, in particular n-Bu4NF, was found to be better fluorinating agent than inorganic fluoride, and 1,3,5-tri-O-benzoyl-alpha -D-ribofuranose-2-trifluoramethylsulphonate ester appeared to be the best substrate. The developed method is suitable for stereospecific (arabino) incorporation of radiofluorine (F-18) into the sugar moiety. (C) 2000 Elsevier Science S.A. All rights reserved.
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页码：87 / 91
页数：5
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