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DOI: 10.1055/s-1996-4314
Synthesis of 2-Chloro-2’-5’-dideoxy-5’-difluoromethylphosphinyladenosine: A Nonhydrolyzable Isosteric, Isopolar Analog of 2-Chlorodeoxyadenosine Monophosphate
Publication History
Publication Date:
31 December 2000 (online)
2-Chloro-2’-5’-dideoxy-5’-difluoromethylphosphinyladenosine (5) was synthesized in thirteen steps from 3-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranoside (1), a carbohydrate which is substituted differently at the 2- and 3-positions, making possible selective deprotection and reductive deoxygenation at the 2’-position of a nucleoside subsequent to glycosylation. Purine nucleoside phosphonate 5 is an analog of the monophosphate ester of the potent, clinically effective immunomodulatory agent 2-chlorodeoxyadenosine (2-CdA), and was synthesized to present a potential means of circumventing drug resistance in target immune cells.
2-chlorodeoxyadenosine - nonhydrolyzable nucleotide analogs - drug resistance - difluoromethyl phosphonates