75145-90-3Relevant articles and documents
Synthesis and Properties of 5'-Deoxynucleoside 5'-Carboxylic Acids and Derivatives
Meyer, Wilfried,Frollmann, Hartmut
, p. 2530 - 2544 (2007/10/02)
A preparative route to 5'-deoxynucleosid-5'-carbonitriles (3), both of the ribose and deoxyribose series, involves crown ether-catalyzed reaction of nucleoside 5'-tosylates with solid potassium cyanide in organic solvents.O2,5'-Cyclo derivatives of pyrimidine nucleosides can also serve as starting materials.The nitriles 3 require acidic conditions for conversion to the esters 6 of 5'-deoxynucleoside 5'-carboxylic acids (7) which are suitable nucleotide models for biochemical studies.In alkaline solutions compounds 3 undergo rapid elimination of the purine or pyrimidine base.Furthermore the adenine derivative 3a, under addition of the unsaturated sugar fragment 10 yields a new nucleoside 12 in which N6 is inserted in a pyrrolidine ring.The circular dichroism spectra of the new compounds reflect strong electronic interaction between polar C-5'-substituents and the chromophores and are in line with those of other C-5'-modified nucleosides.
