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• W4200549857 endingPage "39" @default.
• W4200549857 startingPage "18" @default.
• W4200549857 abstract "Among the C6-halo purine ribonucleosides, the readily accessible 6-chloro derivative has been known to undergo slow SNAr reactions with amines, particularly aryl amines. In this work, we show that in 0.1 M AcOH in EtOH, aryl amines react quite efficiently at the C6-position of 2',3',5'-tri-O-(t-BuMe2Si)-protected 6-chloropurine riboside (6-ClP-riboside), with concomitant cleavage of the 5'-silyl group. These two-step processes proceeded in generally good yields, and notably, reactions in the absence of AcOH were much slower and/or lower yielding. Corresponding reactions of 2',3',5'-tri-O-(t-BuMe2Si)-protected 6-ClP-riboside with alkyl amines proceeded well but without desilylation at the primary hydroxyl terminus. These differences are likely due to the acidities of the ammonium chlorides formed in these reactions, and the role of AcOH was not desilylation but possibly only purine activation. With 50% aqueous TFA in THF at 0 °C, cleavage of the 5'-silyl group from 2',3',5'-tri-O-(t-BuMe2Si)-protected N6-alkyl adenosine derivatives and from 6-ClP-riboside was readily achieved. Reactions of the 5'-deprotected 6-ClP-riboside with alkyl amines proceeded in high yields and under mild conditions. Because these complementary methodologies yielded N6-aryl and -alkyl adenosine derivatives containing a free 5'-hydroxyl group, a variety of product functionalizations were undertaken to yield N6,C5'-doubly modified nucleoside analogues." @default.
• W4200549857 created "2021-12-31" @default.
• W4200549857 creator A5010134206 @default.
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• W4200549857 creator A5073373934 @default.
• W4200549857 creator A5074697800 @default.
• W4200549857 date "2021-12-14" @default.
• W4200549857 modified "2023-10-14" @default.
• W4200549857 title "General Approach to <i>N</i>⁶,C5′-Difunctionalization of Adenosine" @default.
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• W4200549857 cites W1979787483 @default.
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• W4200549857 cites W2003957879 @default.
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• W4200549857 cites W2007554213 @default.
• W4200549857 cites W2013570284 @default.
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• W4200549857 doi "https://doi.org/10.1021/acs.joc.1c01587" @default.
• W4200549857 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/34905365" @default.
• W4200549857 hasPublicationYear "2021" @default.
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