42926-80-7Relevant academic research and scientific papers
METHOD FOR PREPARING 3'-O-AMINO-2'-DEOXYRIBONUCLEOSIDE-5'-TRIPHOSPHATE
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Page/Page column 23, (2020/03/23)
The invention relates to a method for preparing 3 ' -O-amino-2' -deoxyribonucleoside-5 ' - triphosphate. It also relates to a solid support functionalized with at least one N- hydroxyphthalimide moiety and uses thereof for protecting 3 '-hydroxy group of a 2'- deoxyribonucleoside during synthesis of a nucleoside or a derivative thereof.
Tritylation of alcohols under mild conditions without using silver salts
Shahsavari, Shahien,Chen, Jinsen,Wigstrom, Travis,Gooding, James,Gauronskas, Alexander,Fang, Shiyue
supporting information, p. 3877 - 3880 (2016/08/02)
Secondary alcohols were conveniently tritylated under mild conditions within a short running time with tritylium trifluoroacetate generated in situ from trityl alcohols and trifluoroacetic anhydride. No expensive silver salts were needed for the reactions. Four secondary alcohols were tritylated with both mono- and dimethoxy trityl alcohols giving good to excellent isolated yields. The reaction was also tested on four nucleoside derivatives that have primary alcohols. Satisfactory results were also obtained.
Tailoring peptide-nucleotide conjugates (PNCs) for nucleotide delivery in bacterial cells
De, Swarup,Groaz, Elisabetta,Herdewijn, Piet
, p. 2322 - 2348 (2014/04/17)
The design and synthesis of peptide-2′-deoxythymidine-5′-O- monophosphate conjugates as potential active delivery systems for nucleotides into auxotrophic E. coli strains is presented. A series of oligopeptides were allowed to react with 5′-O-(dibenzylphosphate)-2′-deoxythymidine or its suitably 3′-derivatized analogues to give the relevant peptide-nucleotide adducts, by the formation of a biolabile chemical connection. Using strategies based on the principles of orthogonal protection and activation, rational variations were made to the linker and the peptide moiety in order to tune the metabolic stability of the conjugates.
An efficient and selective method for the preparation of triphenylmethyl ethers of alcohols and nucleosides
Zekri, Negar,Alamdari, Reza Fareghi
experimental part, p. 563 - 568 (2010/08/05)
A very simple and efficient method is described for the protection of alcohols and nucleosides with benzyl monomethoxytrityl and benzyl dimethoxytrityl ethers in the presence of diethylazodicarboxylate and a catalytic amount of ceric triflate. High selectivity was observed for the tritylation of 5'-OH function of nucleosides.
A solvent free and selective method for preparation of triphenylmethyl ethers of alcohols and nucleosides
Zekri, Negar,Alamdari, Reza Fareghi,Khalafi-Nezhad, Ali
experimental part, p. 299 - 304 (2012/04/23)
A very simple and efficient method is described for protection of alcohols and nucleosides with trityl(triphenylmethyl), mono and dimethoxytrityl chlorides in the presence of triethylamine under microwave irradiation. High selectivity was observed for tritylation of 5'-OH function of nucleosides.
A base-stable dithiomethyl linker for solid-phase synthesis of oligonucleotides
Semenyuk, Andrey,Kwiatkowski, Marek
, p. 469 - 472 (2008/02/04)
A novel linkage, useful for the synthesis of oligonucleotides is described. The linking function is compatible with all conditions used for oligonucleotide synthesis, orthogonal to all other protecting groups, but regenerates 3′-OH rapidly upon mild reduc
Towards new boron carriers for boron neutron capture therapy: Metallacarboranes and their nucleoside conjugates
Lesnikowski, Zbigniew J.,Paradowska, Edyta,Olejniczak, Agnieszka B.,Studzinska, Miroslawa,Seekamp, Petra,Schuessler, Uw,Gabel, Detlef,Schinazi, Raymond F.,Plesek, Jaromir
, p. 4168 - 4175 (2007/10/03)
Thymidine conjugates containing metallacarborane, {8-[5-(N 3-thymidine)-3-oxa-pentoxy]-3-cobalt bis(1,2-dicarbollide)} - (5) and {8-[5-(O4-thymidine)-3-oxa-pentoxy]-3-cobalt bis(1,2-dicarbollide)}- (6) ions and
Tetrabutylammonium bromide: An efficient media for dimethoxytritylation of the 5'-hydroxyl function of nucleosides
Khalafi-Nezhad, Ali,Mokhtari, Babak
, p. 6737 - 6739 (2007/10/03)
An efficient procedure for selective dimethoxytritylation of the 5'-hydroxyl function of nucleosides in the presence of DABCO in molten tetrabutylammonium bromide is described. The methodology is very practical, environmentally benign and produced the desired product in less than 5 min by grinding in a hot mortar. In addition, the effects of the room temperature ionic liquid (1-butyl-3-methylimidazolium chloride) and microwave irradiation on this system were also studied and the results showed that depurination of the nucleosides occurred under microwave irradiation.
Preparation of 4'-substituted thymidines by substitution of the thymidine 5'-esters.
Jung,Toyota
, p. 2624 - 2635 (2007/10/03)
tert-Butyl thymidylate 3 was prepared from thymidine 1 in six steps and 67% overall yield. When the lithium trianion of 3 (prepared by treatment of 3 with excess LDA and then excess tert-butyllithum) is reacted with electrophiles, trapping occurs stereoselectively from either the alpha- or beta-face depending on the electrophile (Scheme 1). Deuterioacetic acid in deuteriomethanol affords mainly the alpha-deuterated product (4a/4b = 2.4:1) while all other electrophiles, e.g., phenylselenenyl chloride, allyl bromide, and N-fluorobenzenesulfonimide (NFSI), give predominately (or completely) the products of attack from the beta-face (5bcd/4bcd = 3.7:1 to 100:0). The structures of the products were determined by coupling constant analysis of both the initial compounds and the diols 6bcd prepared by ester reduction and by formation of the acetonides 7bc. The methyl ester of the 3'-epimer of thymidylic acid 9 was also prepared from thymidine 1 in nine steps and 74% overall yield. When the lithium trianion of 9 (prepared by treatment of 9 with excess LDA and then excess tert-butyllithum) is reacted with electrophiles, trapping also occurs stereoselectively with attack on either the alpha- or beta-face depending on the electrophile (Scheme 2). Again, deuterioacetic acid in deuteriomethanol affords mainly the beta-deuterated product (11a/10a = 1.6:1) while all other electrophiles, e.g., phenylselenenyl chloride, methyl iodide, allyl bromide, and NFSI, gave predominately (or completely) the product of attack from the alpha-face (8.7:1 to 100: 0). Again, the structures of the products were determined by coupling constant analysis of both the initial compounds, and the diols 12b-e were prepared by reduction of the ester and by formation of the acetonides 13bcd. A rationale has been developed using molecular mechanics calculations to explain the diastereoselectivity that involves staggered axial attack on the sp(2) carbon opposite to the pseudoaxial alkoxy group in the most stable half-chair conformation of the enolates, as shown in Schemes 3-5.
Incorporation of positively charged deoxynucleic S-methylthiourea linkages into oligodeoxyribonucleotides
Challa, Hemavathi,Bruice, Thomas C
, p. 2423 - 2427 (2007/10/03)
Oligodeoxyribonucleic acids (15- and 18-mers) containing both negatively charged phosphate and positively charged S-methyl thiourea internucleoside linkages (DNmt/DNA chimera) have been synthesized. DNA binding characteristics and nuclease resistance of DNmt/DNA chimera have been evaluated.
