1182206-91-2Relevant academic research and scientific papers
Oligonucleotide analogues with integrated bases and backbone: Part 20 - Hydrazide- and amide-linked analogues. 1. Design and synthesis of monomeric building blocks
Peifer, Manuel,De Giacomo, Fabio,Schandl, Martin,Vasella, Andrea
experimental part, p. 1134 - 1166 (2009/10/17)
Hydrazide- and amide-linked oligonucleoside analogues with integrated bases and backbone were designed to allow for a rapid synthesis of long and water-soluble oligomers. The uracil-, cytosine-, and adenine-derived hydrazide building blocks 13-15 were synthesized by nucleophilic substitution with the hydrazine 23 of the halides 19, 28, and 34, derived from the alcohols 18, 27, and 33, respectively, while the uracil-, cytosine-, and adenine-derived amide building blocks 45-47 were synthesized by a Curtius degradation of the carboxylic acids 51, 56, and 61. These acids were obtained by Wittig reaction of the aldehydes 49, 53, and 58. The guanine-derived monomers 44 and 48 were synthesized by reductive cyclisation of the nitroso amides 38 and 63, respectively, resulting from acylation of the known 2,6-diamino-4-(benzyloxy)-5- nitrosopyrimidine (37).
