69504-07-0Relevant articles and documents
Synthesis and antibacterial activity of 5′-tetrachlorophthalimido and 5′-azido 5′-deoxyribonucleosides
Van Ostrand, Robert,Jacobsen, Casey,Delahunty, Alicia,Stringer, Carley,Noorbehesht, Ryan,Ahmed, Haidi,Awad, Ahmed M.
, p. 181 - 197 (2017/02/15)
Reported is an efficient synthesis of adenyl and uridyl 5′-tetrachlorophthalimido-5′-deoxyribonucleosides, and guanylyl 5′-azido-5′-deoxyribonucleosides, which are useful in solid-phase synthesis of phosphoramidate and ribonucleic guanidine oligonucleotides. Replacement of 5′-hydroxyl with tetrachlorophthalimido group was performed via Mitsunobu reaction for adenosine and uridine. An alternative method was applied for guanosine which replaced the 5′-hydroxyl with an azido group. The resulting compounds were converted to 5′-amino-5′-deoxyribonucleosides for oligonucleotide synthesis. Synthetic intermediates were tested as antimicrobials against six bacterial strains. All analogs containing the 2′,3′-O-isopropylidine protecting group demonstrated antibacterial activity against Neisseria meningitidis, and among those analogs with 5′-tetrachlorophthalimido and 5′-azido demonstrated increased antibacterial effect.
Synthesis of 2'-O-substituted ribonucleosides.
Serebryany,Beigelman
, p. 1007 - 1009 (2007/10/03)
An efficient synthesis of 2'-O-substituted ribonucleosides, including 2'-O-TBDMS and 2'-O-TOM protected as well as 2'-O-Me and 2'-O-allyl derivatives is presented. Di-t-butylsilylene group was employed for simultaneous protection of 3'- and 5'- hydroxyl functions of nucleoside on the first step. Subsequent silylation or alkylation of free 2'-OH followed by introduction of suitable protection on the base moiety and removal of cyclic silyl protection gave target compounds in a high yield.
Aqueous trichloroacetic acid: Another useful reagent for highly selective 5′-desilylation of multisilylated nucleosides
Zhu, Xue-Feng,Williams, Howard J.,Scott, A. Ian
, p. 2011 - 2016 (2007/10/03)
Highly selective 5′-desilylation of multisilylated nucleosides can be achieved in excellent yield by treatment with 4.2 M aqueous trichloroacetic acid:THF (1:4) at 0°C.
An efficient preparation of protected ribonucleosides for phosphoramidite RNA synthesis
Serebryany, Vladimir,Beigelman, Leonid
, p. 1983 - 1985 (2007/10/03)
An efficient synthesis of protected ribonucleosides useful for phosphoramidite RNA synthesis is described. Di-t-butylsilylene group was employed for simultaneous protection of 3′- and 5′-hydroxyl functions of nucleoside. Subsequent silylation of free 2′-O
Facile and highly selective 5′-desilylation of multisilylated nucleosides
Zhu, Xue-Feng,Williams, Howard J.,Ian Scott
, p. 2305 - 2306 (2007/10/03)
The facile and highly selective 5′-desilylation of multisilylated nucleosides was discussed. The selective 5′-desilylation using aqueous acetic acid can be improved if THF is added as a co-solvent. It was found that the use of THF increases the solubility
