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Syntheses of [2-2H]-5-ethynyl-1-(β-D-ribofuranosyl)imidazole-4-carboxamide and 5-ethynyl-1-([5-3H]-β-D-ribofuranosyl)imidazole-4-carboxamide (EICAR)

✍ Scribed by Noriaki Minakawa; Akira Matsuda; Zuping Xia; Leonard I. Wiebe; Edward E. Knaus

Publisher: John Wiley and Sons
Year: 1996
Tongue: French
Weight: 654 KB
Volume: 38
Category: Article
ISSN: 0022-2135
DOI: 10.1002/(sici)1099-1344(199609)38:9<809::aid-jlcr899>3.0.co;2-0

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✦ Synopsis

Metallation of 5-ethynyl-1-(2,3,5-tri-O-terf-butyldimethylsilyl-~-~-ribof~anosyl)imidazole-4-carboxamide (1) using n-BuLi, deuteration with deuterium oxide and removal of the fertbutyldimethylsilyl protecting groups using tetrabutylammonium fluroide yielded [2-'H]-5ethynyl-1 -(~-D-ribofi1ranosyl)imidazole-4-carboxamide (5a. 75 atom % deuterium). Regiospecific deprotection of the masked aldehyde N,h"-diphenyfethylenediamino synthon -14 using DIAION PK212 ion-exchange resin (H' form) yielded the aldehyde derivative (15). Reduction of the aldehyde moiety of 15 using excess ['HINaBH, gave the carbinol product -17. Removal of the ribohanosyl 2,3-isopropylidene protecting group from 17 using 90% trifluoroacetic acid afforded 5-ethynyl-1 -([5-3H]-~-~-ribo~ranosyl)imidazole-4-carboxamide (18, 19% chemical yield, > 99% radiochemical purity, specific activity 1.56 Ci/mmol).

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