A Diastereoselective Method for the Construction of syn-2′-Deoxy-2′-fluoronucleosides

A general and diastereoselective fluorination/glycosylation strategy for the synthesis of 2′-fluorinated nucleosides has been developed. Electrophilic fluorination of a glycal with NFSI provided the 1′,2′-difunctionalized furanoside intermediate with high diastereoselectivity. The TBS-protected 2′-d...

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Published inOrganic letters Vol. 24; no. 27; pp. 4860 - 4864
Main Authors Pirnot, Michael T., Mao, Edna, Lam, Yu-hong, Limanto, John, Cohen, Ryan D., Chung, Cheol K., Phillips, Eric M.
Format Journal Article
LanguageEnglish
Published American Chemical Society 15.07.2022
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Summary:A general and diastereoselective fluorination/glycosylation strategy for the synthesis of 2′-fluorinated nucleosides has been developed. Electrophilic fluorination of a glycal with NFSI provided the 1′,2′-difunctionalized furanoside intermediate with high diastereoselectivity. The TBS-protected 2′-deoxyfluorosulfonimide sugar was prepared on an 80 g scale and isolated as a crystalline, bench-stable single diastereomer. This intermediate was found to undergo a subsequent glycosylation reaction with a variety of heteroaryl nucleophiles with generally good diastereoselectivities.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01561