857447-79-1

Upstream product

• 5574-97-0 tetrabutylammonium dihydrogen phosphate 
• 2052-49-5 tetra(n-butyl)ammonium hydroxide 

Relevant academic research and scientific papers

Synthesis of Modified Nucleoside Oligophosphates Simplified: Fast, Pure, and Protecting Group Free

Phosphoramidite analogues of modified cyclotriphosphates provide a general and step-economical synthesis of nucleoside triphosphates and analogues on scale without the need for protecting groups. These reagents enable rapid access to pure nucleoside oligophosphates and a range of other analogues that were previously difficult to obtain (e.g., NH, CH2, CCl2, and CF2 replacements for O, phosphono- and phosphoimidazolides, -morpholidates, -azidates, and -fluoridates). DFT calculations demonstrate that the selectivity of the cyclotriphosphate opening reactions proceeds via an in-line substitution mechanism that displaces the least charged leaving group.

Efficient Automated Solid-Phase Synthesis of DNA and RNA 5′-Triphosphates

A fast, high-yielding and reliable method for the synthesis of DNA- and RNA 5′-triphosphates is reported. After synthesizing DNA or RNA oligonucleotides by automated oligonucleotide synthesis, 5-chloro-saligenyl-N,N-diisopropylphosphoramidite was coupled to the 5′-end. Oxidation of the formed 5′-phosphite using the same oxidizing reagent used in standard oligonucleotide synthesis led to 5′-cycloSal-oligonucleotides. Reaction of the support-bonded 5′-cycloSal-oligonucleotide with pyrophosphate yielded the corresponding 5′-triphosphates. The 5′-triphosphorylated DNA and RNA oligonucleotides were obtained after cleavage from the support in high purity and excellent yields. The whole reaction sequence was adapted to be used on a standard oligonucleotide synthesizer.

Sulfonyl imidazolium salts as reagents for the rapid and efficient synthesis of nucleoside polyphosphates and their conjugates

A procedure for the synthesis of nucleoside polyphosphates and their conjugates using sulfonylimidazolium salts as key reagents is described. The procedure is rapid and high yielding, does not require prior protection and subsequent deprotection of the donors or acceptors, and can be used to activate nucleoside mono-, di- and triphosphates, and a wide variety of acceptors and donors can be used.

"RS+" as a coupling reagent for phosphorylation and carboxylic acid activation

Phenylsulfenyl chloride, a sulfenium ion transfer reagent, promotes the formation of pyrophosphate from tetrabutylammonium phosphate, under controlled "pH" conditions, in yields of up to 85%. Dichloroacetic and succinic acids, in the presence of phenylsulfenyl chloride and a tertiary amine, form the corresponding anhydrides in very good yields. The treatment of dichloroacetic acid or p-nitrobenzoic acid with phenylsulfenyl chloride in the presence of a tertiary amine, followed by the addition of aniline, affords the corresponding anilides in yields of up to 42%.