Nucleic Acid Related Compounds. 80. Synthesis of 5'-S-(Alkyl and aryl)-5'-fluoro-5'-thioadenosines with Xenon Difluoride or (Diethylamido) sulfur Trifluoride, …

…, KB Mullah, NK Dalley, CS Yuan, Y Lee…

Index: Robins; Wnuk; Mullah; Dalley; Yuan; Lee; Borchardt Journal of Organic Chemistry, 1994 ,  vol. 59,  # 3  p. 544 - 555

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Citation Number: 32

Abstract

Treatment of 5'-S-(alkyl and aryl)-5'-thioadenosine derivatives 2 with XeF2, or the corresponding sulfoxides 3 with DAST/SbC13, gave diastereomeric 5'-flUOrO compounds which were deprotected to give the 5'-S-(alkyl and aryl)-5 '-fluoro-5'-thioadenosine analogues 5. Stereochemistry was established by X-ray crystallography, and 19F NMR chemical shifts were definitive for configurationally-related 5'-flUOr0 diastereomers. ...