81246-80-2

Usage

Uses

Used in Organic Synthesis:
5'-O-DMT-2'-TBDMS-Uridine is used as a key intermediate in the synthesis of nucleoside analogs for various applications, including pharmaceutical development and materials science. Its unique structure allows for selective protection and deprotection steps, facilitating the synthesis of complex nucleoside derivatives.
Used in Pseudorotaxane Architectures:
In supramolecular chemistry, 5'-O-DMT-2'-TBDMS-Uridine is used as a building block in the preparation of pseudorotaxane architectures. Pseudorotaxanes are supramolecular assemblies where one or more cyclic molecules are threaded through a linear molecule, held together by non-covalent interactions. The use of this nucleoside derivative in pseudorotaxane formation can lead to the development of novel materials with unique properties and potential applications in various fields.
Used in Microwave-Assisted Phosphitylation:
5'-O-DMT-2'-TBDMS-Uridine can undergo microwave-assisted phosphitylation, a key step in the preparation of nucleoside phosphoramidites. Nucleoside phosphoramidites are essential components in the synthesis of oligonucleotides, which are used in various applications such as DNA sequencing, diagnostics, and therapeutics. The use of microwave-assisted phosphitylation can improve the efficiency and yield of this process, leading to the production of high-quality nucleoside phosphoramidites.

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 81246-79-9 5'-dimethoxytrityluridine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 54925-71-2 2'-O-(tert-butyldimethylsilyl)uridine 
• 58-96-8 uridine 
• 144490-31-3 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)uridine-3'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite 
• 97219-04-0 3',5'-O-(di-tert-butylsilanediyl)uridine 
• 146668-79-3 tert-butyldimethylsilyl nitrate 
• 212375-92-3 2’-O-(tert-butyldimethylsilyl)-3’-5’-O-(di-tert-butylsilylene)-uridine 

Downstream Products

• 81279-40-5 4-tetrazolo-1-(β-D-5'-dimethoxytrityl-2'-tert-butyldimethyl silyl ribofuranosyl)-2(1H)-pyrimidinone 3'-p-chlorophenyl β-cyanoethyl phosphotriester 
• 115259-93-3 2'-O-tert-butyldimethylsilyl-5'-O-dimethoxytrityl-3'-O-mesyluridine 
• 127553-47-3 5'-O-DMTr-2'-O-TBDMS-uridine-3'-O-(2-chlorophenyl)phosphate triethylammonium salt 
• 86327-54-0 Imidazole-1-carbothioic acid O-[(2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester 
• 86234-41-5 Thiocarbonic acid O-[(2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester O-phenyl ester 
• 121469-98-5 C₅₉H₆₃N₄O₁₇PSi 
• 154665-03-9 5′-O-(4,4′-dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-4-(2-cyanoethylthio)uridine 
• 82444-92-6 Phosphoric acid (2R,3R,4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-5-(2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 4-chloro-phenyl ester 2-cyano-ethyl ester 
• 82444-82-4 4-(1,2,4-triazol-1-yl)-1-<5'-O-(dimethoxytrityl)-3'-O-((p-chlorophenoxy)(2-cyanoethoxy)phosphoryl)-2'-O-(tert-butyldimetylsilyl)-β-D-ribofuranosyl>pyrimidin-2-(1H)-one 
• 866219-08-1 C₄₇H₅₆N₃O₉PSi 
• 866219-02-5 C₄₇H₅₆N₃O₉PSi 
• 1309592-43-5 5'-DMTr-2'-TBDMS-3'-levulinyl-uridine 
• 180681-97-4 5'-O-(4,4'-dimethoxytrityl)-2'-(tert-butyldimethylsilyl)uridin-3'-yl hydrogen-phosphonothioate, triethylammonium salt 
• 120401-09-4 C₃₆H₄₄PO₁₀N₂Si^(1-)*C₆H₁₆N⁽¹⁺⁾ 

Relevant academic research and scientific papers

5’-Phosphorylation Increases the Efficacy of Nucleoside Inhibitors of the DNA Repair Enzyme SNM1A

Certain cancers exhibit upregulation of DNA interstrand crosslink repair pathways, which contributes to resistance to crosslinking chemotherapy drugs and poor prognoses. Inhibition of enzymes implicated in interstrand crosslink repair is therefore a promising strategy for improving the efficacy of cancer treatment. One such target enzyme is SNM1A, a zinc co-ordinating 5’–3’ exonuclease. Previous studies have demonstrated the feasibility of inhibiting SNM1A using modified nucleosides appended with zinc-binding groups. In this work, we sought to develop more effective SNM1A inhibitors by exploiting interactions with the phosphate-binding pocket adjacent to the enzyme's active site, in addition to the catalytic zinc ions. A series of nucleoside derivatives bearing phosphate moieties at the 5’-position, as well as zinc-binding groups at the 3’-position, were prepared and tested in gel-electrophoresis and real-time fluorescence assays. As well as investigating novel zinc-binding groups, we found that incorporation of a 5’-phosphate dramatically increased the potency of the inhibitors.

Practical silyl protection of ribonucleosides

Herein we report the site-selective silylation of the ribonucelosides. The method enables a simple and efficient procedure for accessing suitably protected monomers for automated RNA synthesis. Switching to the opposite enantiomer of the catalyst allows f

Catalyst recognition of cis-1,2-diols enables site-selective functionalization of complex molecules

Carbohydrates and natural products serve essential roles in nature, and also provide core scaffolds for pharmaceutical agents and vaccines. However, the inherent complexity of these molecules imposes significant synthetic hurdles for their selective functionalization and derivatization. Nature has, in part, addressed these issues by employing enzymes that are able to orient and activate substrates within a chiral pocket, which increases dramatically both the rate and selectivity of organic transformations. In this article we show that similar proximity effects can be utilized in the context of synthetic catalysts to achieve general and predictable site-selective functionalization of complex molecules. Unlike enzymes, our catalysts apply a single reversible covalent bond to recognize and bind to specific functional group displays within substrates. By combining this unique binding selectivity and asymmetric catalysis, we are able to modify the less reactive axial positions within monosaccharides and natural products.

RNA synthesis via dimer and trimer phosphoramidite block coupling

The solid-phase synthesis of oligoribonucleotides using dimer and trimer phosphoramidite blocks is described. This method significantly reduces the total number of steps required in the synthesis of a target RNA sequence, provides more material, and simpl

Synthesis of cyclic di-nucleotidic acids as potential inhibitors targeting diguanylate cyclase

Five analogs of cyclic di-nucleotidic acid including c-di-GMP were synthesized and evaluated for their biological activities on Slr1143, a diguanylate cyclase of Synechocystis sp. Slr1143 was overexpressed from the recombinant plasmid which contained the gene of interest and subsequently purified by affinity chromatography. A new HPLC method capable of separating the compound and product peaks with good resolution was optimized and applied to the analysis of the compounds. Results obtained show that cyclic di-inosinylic acid 1b demonstrates a stronger inhibition on Slr1143 than c-di-GMP and is a potential inhibitor for biofilm formation.

Synthesis of 2'-O-substituted ribonucleosides.

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.

An efficient preparation of protected ribonucleosides for phosphoramidite RNA synthesis

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

Methods for synthesizing nucleosides, nucleoside derivatives and non-nucleoside derivatives

The present invention provides methods for the chemical synthesis of nucleosides and derivatives thereof, including 2′-amino, 2′-N-phthaloyl, 2′-O-methyl, 2′-O-silyl, 2′OH nucleosides, C-nucleosides, nucleoside phosphoramidites, C-nucleoside phosphoramidites, and non-nucleoside derivatives.

Methods for synthesizing nucleosides, nucleoside derivatives and non-nucleoside derivatives

The present invention provides methods for the chemical synthesis of nucleosides and derivatives thereof, including 2′-amino, 2′-N-phthaloyl, 2′-O-methyl, 2′-O-silyl, 2′-O-triisopropylsilyloxymethyl, 2′-OH nucleosides, C-nucleosides, nucleoside phosphoramidites, C-nucleoside phosphoramidites, and non-nucleoside derivatives.

Nucleoside recovery in DNA and RNA synthesis

Nucleoside phosphoramidites and H-phosphonate diesters can be converted to nucleosides under mild conditions and in high yields by reaction with polyhydroxy alcohols.