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Synthesis of certain pyrazolo[3,4‐ d ]pyrimidin‐3‐one nucleosides
Author(s) -
Anderson Jack D.,
Cottam Howard B.,
Larson Steven B.,
Dee Nord L.,
Revankar Ganapathi R.,
Robins Roland K.
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270262
Subject(s) - chemistry , boron trifluoride , pyrimidine , guanosine , inosine , stereochemistry , ribonucleoside , uracil , glycosylation , sodium iodide , iodide , organic chemistry , catalysis , enzyme , dna , rna , biochemistry , gene
Synthesis of the pyrazolo[3,4‐ d ]pyrimidin‐3‐one congeners of guanosine, adenosine and inosine is described. Glycosylation of 3‐methoxy‐6‐methylthio‐1 H ‐pyrazolo[3,4‐ d ]pyrimidin‐4(5 H )‐one ( 13 ) with 1‐ O ‐acetyl‐2,3,5‐tri‐ O ‐benzoyl‐D‐ribofuranose ( 16 ) in the presence of boron trifluoride etherate gave 3‐methoxy‐6‐methylthio‐1‐(2,3,5‐tri‐ O ‐benzoyl‐β‐D‐ribofuranosyl)pyrazolo[3,4‐ d ]pyrimidin‐4(5 H )‐one ( 17 ) which, after successive treatments with 3‐chloroperoxybenzoic acid and methanolic ammonia, afforded 6‐amino‐3‐methoxy‐1‐β‐D‐ribofuranosylpyrazolo[3,4‐ d ]pyrimidin‐4(5 H )one ( 18 ). The guanosine analog, 6‐amino‐1‐β‐D‐ribofuranosylpyrazolo[3,4‐ d ]pyrimidine‐3,4(2 H ,5 H )‐dione ( 21 ), was made by sodium iodide‐chlorotrimethylsilane treatment of 6‐amino‐3‐methoxy‐1‐(2,3,5‐tri‐ O ‐acetyl‐β‐D‐ribofuranosyl)pyrazolo[3,4‐ d ]pyrimidin‐4(5 H )one ( 19 ), followed by sugar deprotection. Treatment of the adenine analog, 4‐amino‐1 H ‐pyrazolo[3,4‐ d ]pyrimidin‐3(2 H )‐one ( 11 ), according to the high temperature glycosylation procedure yielded a mixture of N‐1 and N‐2 ribosyl‐attached isomers. Deprotection of the individual isomers afforded 4‐amino‐3‐hydroxy‐1‐βribofuranosylpyrazolo‐[3,4‐ d ]pyrimidine ( 26 ) and 4‐amino‐2‐β‐D‐ribofuranosylpyrazolo[3,4‐ d ]pyrimidin‐3(7 H )‐one ( 27 ). The structures of 26 and 27 were established by single crystal X‐ray diffraction analysis. The inosine analog, 1‐β‐D‐ribofuranosylpyrazolo[3,4‐ d ]pyrimidine‐3,4(2 H ,5 H )‐dione ( 28 ), was synthesized enzymatically by direct ribosylation of 1 H ‐pyrazolo[3,4‐ d ]pyrimidine‐3,4(2 H ,5 H )‐dione ( 8 ) with ribose‐1‐phosphate in the presence of purine nucleoside phosphorylase, and also by deamination of 26 with adenosine deaminase.