15958-99-3Relevant academic research and scientific papers
Acyclic Analogs of Nucleosides. Synthesis of Chiral 1,5-Dihydroxy-4-methyl-3-oxapent-2-yl Derivatives of Uracil
Mikhailov, S. N.,Grishko, N. B.
, p. 75 - 78 (1988)
A convenient method has been developed for the synthesis of optically active 1-uracils. 5'-Deoxyuridine is obtained from 2',3'-O-isopropylideneuridine, and its periodate oxidation followed by reduction with sodium tetrahydroborate leads to the desired 4(R),2(R)-isomer.The acetonide of α-uridine is converted into the 4(R),2(S)-isomer analogously.
Black light induced radical cyclization approach to cyclonucleosides: An independent approach
Perchyonok, Victoria T.
, p. 337 - 340 (2011)
The paper highlights an efficient methodology based on consecutive radical reaction for the preparation of cyclonucleoside derivatives. The reactions were performed in organic and aqueous media, using common and efficient free radical hydrogen donors in the range of innovative and conventional initiation conditions to afford good to excellent yields of corresponding cyclonucleosides. The mechanistic aspects of the transformations are also addressed.
A versatile synthesis of 5'-fenctionalized nucleosides through regioselective enzymatic hydrolysis of their peracetylated precursors
Bavaro, Teodora,Rocchietti, Silvia,Ubiali,Filice, Marco,Terreni, Marco,Pregnolato, Massimo
experimental part, p. 1967 - 1975 (2009/09/08)
We describe a chemo-enzymatic synthesis of modified nucleosides through lipase-catalyzed hydrolysis of their peracetylated precursors. It was found from screening of a large number of substrates that these enzymesregioselectivities were affected by the sugar and the nucleobase structures. By selecting the best enzyme for each substrate in terms of activity and regioselectivity, we prepared a small library of differently monodeprotecled purine and pyrimidine nucleosides useful as intermediates for the synthesis of high-value nucleosides and mononucleotides. By this approach, the chemo-enzymatic preparation of doxifluridine (14) and uridine 5'-monophosphate (5'-UMP, 15) from peracetylated uridine 1 was carried out. Elimination of many of the processing stages associated with existing methods was achieved, and higher yields and products of increased purity were generated. Wiley-VCH Verlag GmbH & Co. KGaA.
