153434-31-2Relevant articles and documents
Phosphotriesters Approach to the Synthesis of Oligonucleotides: A Reappraisal
Reese, Colin B.,Pei-Zhuo, Zhang
, p. 2291 - 2302 (2007/10/02)
The phosphotriester approach to the synthesis of oligodeoxyribo- and oligoribo-nucleotides in solution has been reinvestigated.The efficacy of mesitylene-2-sulfonyl chloride (MSCl) 15a, 2,4,6-triisopropylbenzenesulfonyl chloride (TrisCl) 15b, 4-bromobenzenesulfonyl chloride 15c, naphthalene-1-sulfonyl chloride 39, and 2- and 4-nitrobenzenesulfonyl chlorides 40a and 40b, respectively, as activating agents has been examined.The latter arenesulfonyl chlorides have been used in conjunction with the following nucleophilic catalysts: 1-methylimidazole, 3-nitro-1H-1,2,4-triazole 19, 5-(3-nitrophenyl)-1H-tetrazole 20a, 5-(3,5-dinitrophenyl)-1H-tetrazole 20b, 5-(1-methylimidazol-2-yl)-1H-tetrazole 21, 5--1H-tetrazole 22, 4-ethoxypyridine 1-oxide 14a, 4,6-dinitro-1-hydroxybenzotriazole 29a, 1-hydroxy-4-nitro-6-(trifluoromethyl)benzotriazole 29b, 1-hydroxy-5-phenyltetrazole 30a and 1-hydroxy-5-(3-nitrophenyl)tetrazole 30b.The rates of formation and yields of the fully protected dideoxyribonucleoside and diribonucleoside phosphates 37 and 47, respectively, were determined using various combinations of activating agents and nucleophilic catalysts.Although 2- and 4-nitrobenzenesulfonyl chlorides 40a and 40b, respectively, proved to be the most powerful activating agents, their use in the deoxy-series led to the formation of by-products and hence to unsatisfactory isolated yields of the dideoxyribonucleoside phosphate 37.