1025967-67-2Relevant academic research and scientific papers
Design and synthesis of some new α-phenyl cinnamoyl derivatives for selective protection of purine nucleosides
Tripathi, Snehlata,Misra, Krishna,Sanghvi, Yogesh
, p. 3069 - 3081 (2005)
Three new α-phenylcinnamic acid derivatives [4-methoxy-α- phenylcinnamic acid, α-(4-methoxyphenyl)-cinnamic acid, and 4,4′-bismethoxy-α-phenylcinnamic acid] were synthesized, characterized, and selectively used for protecting the exocyclic amino function of purine nucleosides (2′-deoxyadenosine and 2′-deoxyguanosine) via active ester generation. The acids were first activated using p -nitrophenol, and these activated esters were used subsequently for the selective protection of amino groups. The N -protected derivatives of 2′-deoxyguanosine and 2′-deoxyadenosine have been found to be sufficiently stable toward acids, thus minimizing depurination under oligodeoxyribonucleotide synthesis protocol. The ease of syntheses of N -protected purine nucleosides, their stability under an acidic environment, and mild deprotection conditions are the key advantages of the new protecting groups. Copyright Taylor & Francis, Inc.
