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- W2037199021 abstract "Reaction of 2-phenyltrimethinium salt 1 with thiourea and subsequent reaction with chloroacetic acid afforded 5-phenyl-2(1 H )-pyrimidinone ( 3 ). Its silyl derivative 4 was condensed with 1- O -acetyl-2,3,5-tri- O -benzoyl-D-ribofuranose under catalysis with tin tetrachloride or trimethylsilyl trifluoromethanesulfonate to give protected nucleoside 5 together with 5', O 6 -cyclo-5-phenyl-1,3-bis- (β-D-ribofuranosyl)-6-hydroxy-5,6-dihydro-2(1 H ,3 H )-pyrimidinone ( 7 ). The greatest amounts of 7 were formed with the latter catalyst. Nucleosidation of the silyl derivative 4 with protected methyl 2-deoxy-D-ribofuranoside 8 or 2-deoxy-D-ribofuranosyl chloride 9 afforded 1-(2-deoxy-3,5-di- O - p -toluoyl-β-D-ribofuranosyl)-5-phenyl-2(1 H )-pyrimidinone ( 10 ) and its α-anomer 11 . Reaction of 10 and 11 with methanolic ammonia gave free 2'-deoxynucleosides 12 and 13 . Compound 13 was converted into 5'- O - tert -butyldiphenylsilyl-3'- O -mesyl derivative 14 which on heating with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and subsequent cleavage with tetrabutylammonium fluoride afforded 2',3'-dideoxy-2',3'-didehydronucleoside 15 . Reaction of the silyl derivative 4 with 1,2-di- O -acetyl-3,5-di- O -benzoylxylofuranose ( 18 ), catalyzed with tin tetrachloride, furnished 1-(2- O -acetyl-3,5-di- O -benzoyl-β-D-xylofuranosyl)-2(1 H )-pyrimidinone ( 19 ) which was deprotected to give the β-D-xylofuranosyl derivative 22 . As a side product, the nucleosidation afforded the β-D-xylopyranosyl derivative 23 . Deacetylation of compound 19 gave 1-(3,5-di- O -benzoyl-β-D-xylofuranosyl)-5-phenyl-2(1 H )-pyrimidinone ( 24 ) which on reaction with thionyl chloride afforded 2'-chloro-2'-deoxynucleoside 25 and 2', O 6 -cyclonucleoside 26 . Heating of compound 25 with DBU in dimethylformamide furnished the lyxo -epoxide 27 which on reaction with methanolic ammonia was converted into free 1-(2,3-anhydro-β-D-lyxofuranosyl)-5-phenyl-2(1 H )-pyrimidinone ( 28 ). Reaction of 1,2-di- O -acetyl-5- O -benzoyl-3- O -methanesulfonyl-D-xylofuranose ( 30 ) with silyl derivative 4 gave the nucleoside 31 which by treatment with DBU was converted into an equilibrium mixture of 5'-benzoylated arabinofuranoside 33a and its 2',6-anhydro derivative 33b ." @default.
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- W2037199021 date "1996-01-01" @default.
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- W2037199021 title "Synthesis of 5-Phenyl-2(1H)-pyrimidinone Nucleosides" @default.
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- W2037199021 doi "https://doi.org/10.1135/cccc19960458" @default.
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