Journal of labelled compounds and radiopharmaceuticals p. 809 - 824 (1996)
Update date:2022-08-02
Topics:
Minakawa, Noriaki
Matsuda, Akira
Xia, Zuping
Wiebe, Leonard I.
Knaus, Edward E.
Metallation of 5-ethynyl-1-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofura nosyl)imidazole -carboxamide (1) using n-BuLi, deuteration with deuterium oxide and removal of the tert-butyldimethylsilyl protecting groups using tetrabutylammonium fluroide yielded [2-2H]-5-ethynyl- 1-(β-D-ribofuranosyl)imidazole-4-carboxamide (5a, 75 atom % deuterium). Regiospecific deprotection of the masked aldehyde N,N'-diphenylethylenediamino synthon 14 using DIAION PK2I2 ion-exchange resin (H+ form) yielded the aldehyde derivative (15). Reduction of the aldehyde moiety of 15 using excess [3H]NaBH4 gave the carbinol product 17. Removal of the ribofuranosyl 2,3-isopropylidene protecting group from 17 using 90% trifluoroacetic acid afforded 5-ethynyl-1-([5-3H]-β-D-ribofuranosyl)imidazole-4-carboxamide (18. 19% chemical yield, > 99% radiochemical purity, specific activity 1.56 Ci/mmol).
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Doi:10.1021/jacs.0c04533
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(2003)Doi:10.1002/anie.199622261
(1996)Doi:10.1021/ja970251g
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(1996)