165589-89-9

Upstream product

• 69304-38-7 3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 
• 1082068-88-9 5',3'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-1-imidazole thionocarbamate 
• 62-53-3 aniline 
• 103-72-0 phenyl isothiocyanate 

Downstream Products

• 1082068-98-1 2'-O-phenylamine-carbothioate uridine 
• 1219089-76-5 2'-O-(phenylaminecarbothioate)-5'-O-(4,4'-dimethoxytrityl)-uridine-3'-O-(β-cyanoethyl)-N,N-diisopropyl-phosphoramidite 
• 98495-56-8 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxyuridine 

Relevant academic research and scientific papers

Thiocarbon-protecting groups for RNA synthesis

Aspects of the invention include 2'-protected nucleoside monomers that are protected at the 2'-site with thiocarbon protecting groups. Thiocarbon protecting groups of interest include thiocarbonate, thionocarbonate, dithiocarbonate groups, as well as thionocarbamate protecting groups. Aspects of the invention further include nucleic acids that include the protecting groups of the invention, as well as methods of synthesizing nucleic acids using the protecting groups of the invention.

Streamlined process for the chemical synthesis of RNA using 2-O-thionocarbamate-protected nucleoside phosphoramidites in the solid phase

An improved method for the chemical synthesis of RNA was developed utilizing a streamlined method for the preparation of phosphoramidite monomers and a single-step deprotection of the resulting oligoribonucleotide product using 1,2-diamines under anhydrous conditions. The process is compatible with most standard heterobase protection and employs a 2′-O-(1,1-dioxo- 1λ6-thiomorpholine-4-carbothioate) as a unique 2′-hydroxyl protective group. Using this approach, it was demonstrated that the chemical synthesis of RNA can be as simple and robust as the chemical synthesis of DNA.

PROTECTED MONOMER AND METHOD OF FINAL DEPROTECTION FOR RNA SYNTHESIS

A nucleoside monomer that is protected by a thionocarbamate protecting group is provided, as well as a method for making a polynucleotide that uses the same. Also provided is a polynucleotide synthesis method that employs a diamine to deprotect a protected polynucleotide.

Radical-Based Deoxygenation of Aliphatic Alcohols via Thioxocarbamate Derivatives

N-Phenylthioxocarbamates, obtained from the reaction of alcohols with phenyl isothiocyanate in the presence of NaH, were reduced with various silanes such as triethylsilane, triphenylsilane, and tris(trimethylsilyl)silane, as well as tributylstannane under radical conditions to give deoxygenated products of the corresponding alcohols in excellent yields.The reaction was applicable to not only simple aliphatic alcohols but also sugars and nucleosides.Regio- and stereoselective deuteration using deuteriosilanes and deuteriostannane was also examined under the similar conditions.