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.

引用

页码：87 / 91

页数：5

共 27 条

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Alauddin, MM
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Prakash, GKS
Watanabe, KA
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JOURNAL OF NUCLEAR MEDICINE, 2000, 41 (05) : 42P - 43P
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Appl. Radiat. Isot., 1 (61-66):
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JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (15): : 8589 - 8595
[7] Enzymatic synthesis and biodistribution in mice of β-O-D-galactopyranosyl-(1,4′)-2′-[1 18F]fluoro-2′-deoxy-D-glucopyranose (2′-[18F]fluorodeoxylactose)
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[8] RIBOFURANOSE DERIVATIVES FROM 3,5-DI-O-BENZOYL-D-RIBOSYL CHLORIDE .1. 1,3,5-TRI-O-BENZOYL-BETA-D-RIBOSE AND 5-O-BENZOYL-1,2,3-O-BENZYLIDYNE-ALPHA-D-RIBOSE
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JOURNAL OF ORGANIC CHEMISTRY, 1957, 22 (11): : 1465 - 1469
[9] An investigation on stereospecific fluorination at the 2′-arabino-position of a pyrimidine nucleoside: radiosynthesis of 2′-deoxy-2′-[18F]fluoro-5-methyl-1-β-D-arabinofuranosyluracil
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NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2009, 28 (5-7): : 678 - 694

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