153631-19-7

Usage

Uses

Used in Pharmaceutical Industry:
1-((2R,3R,4R,5R)-5-((bis(4-Methoxyphenyl)(phenyl)Methoxy)Methyl)-4-hydroxy-3-Methoxytetrahydrofuran-2-yl)-5-MethylpyriMidine-2,4(1H,3H)-dione is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and functional groups make it a promising candidate for the development of new drugs, particularly those targeting specific biological receptors or enzymes.
Used in Chemical Research:
In the field of chemical research, 1-((2R,3R,4R,5R)-5-((bis(4-Methoxyphenyl)(phenyl)Methoxy)Methyl)-4-hydroxy-3-Methoxytetrahydrofuran-2-yl)-5-MethylpyriMidine-2,4(1H,3H)-dione serves as a valuable tool for studying the properties and reactivity of complex organic molecules. Its synthesis and modification can provide insights into the development of new synthetic methods and the exploration of novel chemical reactions.
Used in Drug Delivery Systems:
Similar to gallotannin, 1-((2R,3R,4R,5R)-5-((bis(4-Methoxyphenyl)(phenyl)Methoxy)Methyl)-4-hydroxy-3-Methoxytetrahydrofuran-2-yl)-5-MethylpyriMidine-2,4(1H,3H)-dione can be employed in the development of drug delivery systems. Its structural features may allow for the design of targeted drug carriers, improving the bioavailability and therapeutic efficacy of various pharmaceutical agents.
Used in the Synthesis of Nucleic Acids:
As a uridine-derived oligonucleoside, 1-((2R,3R,4R,5R)-5-((bis(4-Methoxyphenyl)(phenyl)Methoxy)Methyl)-4-hydroxy-3-Methoxytetrahydrofuran-2-yl)-5-MethylpyriMidine-2,4(1H,3H)-dione can be utilized in the synthetic preparation of nucleic acids, such as DNA and RNA. Its incorporation into synthetic nucleic acid sequences may have applications in molecular biology, gene therapy, and the development of new diagnostic tools.

Upstream product

• 109-88-6 magnesium methanolate 
• 817623-11-3 2,2'-anhydro-1-[2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-arabinofuranosyl-5-methyluridine] 
• 1463-10-1 5-Methyluridine 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 153631-17-5 3-(2-cyanoethyl)-1-<5-O--β-D-ribofuranosyl>-5-methyl-1-1H,3H-pyrimidine-2,4-dione 
• 138239-62-0 1-((2R,3R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3,4-dihydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 
• 65-71-4 thymin 
• 3180-76-5 2',3',5'-tri-O-benzoyluridine 
• 163759-44-2 1-<2'-O-Acetyl-3',5'-bis-O-(2,4-dichlorobenzyl)-β-D-ribofuranosyl>-3-<(benzyloxy)methyl>thymin 
• 168427-40-5 3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-4-(2,4-dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-methoxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 163759-45-3 3-<(Benzyloxy)methyl>-1-<3',5'-bis-O-(2,4-dichlorobenzyl)-β-D-ribofuranosyl>thymin 
• 163759-43-1 1-<2'-O-Acetyl-3',5'-bis-O-(2,4-dichlorobenzyl)-β-D-ribofuranosyl>thymin 
• 168427-64-3 1-[(2R,3R,4R,5R)-4-(2,4-Dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-methoxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 163759-40-8 methyl 2,3,5-tris-O-(2,4-dichlorobenzyl)-β-D-ribofuranoside 

Downstream Products

• 199581-44-7 Thiocarbonic acid O-[(2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester O-(3-tert-butyl-phenyl) ester 
• 719302-94-0 5'-O-(4,4'-dimethoxytrityl)-3'-O-(4-methylphenoxy)thiocarbonyl-2'-O-methyl-5-methyluridine 
• 199581-51-6 (2S,3R,4R,5R)-5-(4-Amino-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-tetrahydro-furan-3-carbaldehyde 
• 1055036-95-7 C₄₈H₅₄N₅O₁₇P 
• 318246-97-8 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-3'-deoxy-3'-C-styryl-5-methyluridine 
• 198703-60-5 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-3'-deoxy-3'-C-formyl-5-methyluridine 
• 183737-17-9 3'-de(oxyphosphinico)-3'-[methylene(methylimino)]-5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-methyl-5-methyluridylyl-(3'->5')-2'-O-methyl-5-methyluridine 

Relevant academic research and scientific papers

Synthesis and Multiple Incorporations of 2′-O-Methyl-5-hydroxymethylcytidine, 5-Hydroxymethylcytidine and 5-Formylcytidine Monomers into RNA Oligonucleotides

The synthesis of 2′-O-methyl-5-hydroxymethylcytidine (hm5Cm), 5-hydroxymethylcytidine (hm5C) and 5-formylcytidine (f5C) phosphoramidite monomers has been developed. Optimisation of mild post-synthetic deprotection conditions enabled the synthesis of RNA containing all four naturally occurring cytosine modifications (hm5Cm, hm5C, f5C plus 5-methylcytosine). Given the considerable interest in RNA modifications and epitranscriptomics, the availability of synthetic monomers and RNAs containing these modifications will be valuable for elucidating their biological function(s).

2′-: O -Methyl- and 2′- O -propargyl-5-methylisocytidine: Synthesis, properties and impact on the isoCd-dG and the isoCd-isoGd base pairing in nucleic acids with parallel and antiparallel strand orientation

Oligonucleotides containing 2′-O-methylated 5-methylisocytidine (3) and 2′-O-propargyl-5-methylisocytidine (4) as well as the non-functionalized 5-methyl-2′-deoxyisocytidine (1b) were synthesized. MALDI-TOF mass spectra of oligonucleotides containing 1b are susceptible to a stepwise depyrimidination. In contrast, oligonucleotides incorporating 2′-O-alkylated nucleosides 3 and 4 are stable. This is supported by acid catalyzed hydrolysis experiments performed on nucleosides in solution. 2′-O-Alkylated nucleoside 3 was synthesized from 2′-O-5-dimethyluridine via tosylation, anhydro nucleoside formation and ring opening. The corresponding 4 was obtained by direct regioselective alkylation of 5-methylisocytidine (1d) with propargyl bromide under phase-transfer conditions. Both compounds were converted to phosphoramidites and employed in solid-phase oligonucleotide synthesis. Hybridization experiments resulted in duplexes with antiparallel or parallel chains. In parallel duplexes, methylation or propargylation of the 2′-hydroxyl group of isocytidine leads to destabilization while in antiparallel DNA this effect is less pronounced. 2′-O-Propargylated 4 was used to cross-link nucleosides and oligonucleotides to homodimers by a stepwise click ligation with a bifunctional azide.

Sugar conformational effects on the photochemistry of thymidylyl(3′-5′)thymidine

The synthesis and conformational analysis of 2′-O,5-dimethyluridylyl(3′-5′)-2′-O,5-dimethyluridine (1a), the analogue of thymidylyl(3′-5′)thymidine (TpT; 1b) in which a methoxy group replaces each 2′-α-hydrogen atom, are described. In comparison with TpT, such modification increases the population of the C3′-endo conformer of the sugar ring puckering at the 5′- and 3′-ends from 30 to 75% and from 37 to 66%, respectively. Photolyses of 1a and TpT at 254 nm are qualitatively comparable (the cis-syn cyclobutane pyrimidine dimer and the (6-4) photoproduct are formed), although it is significantly faster in the case of 1a. These results are explained by the increased propensity of the modified dinucleotide to adopt a base-stacked conformation geometry reminiscent of that for TpT.

Antisense inhibition of ras gene with chimeric and alternating oligonucleotides

Compositions and methods are provided for the modulation of expression of the human ras gene in both the normal and activated forms. Oligonucleotides are provided that have methylene(methylimino) linkages alternating with phosphorothioate or phosphodiester linkages. Further oligonucleotides are provide that have a first region having a methylene(methylimino) linkage alternating with a phosphorothioate or phosphodiester linkage and a second region having phosphorothioate linkages. Such oligonucleotides can be used for diagnostics as well as for research purposes including methods for diagnosis, detection and treatment of conditions arising from the activation of the H-ras gene.

An efficient multigram synthesis of monomers for the preparation of novel oligonucleotides containing isosteric non-phosphorous backbones

The facile preparation of two novel classes of nucleoside analogs for the inclusion as dimeric non-phosphorous containing subunits in chime fie backbones has been accomplished. The concise preparation of 3'- formylnucleosides and 5'-O-(N-methylhydroxylamino)-nucleosides is reported.

38. A new access to 2'-O-alkylated ribonucleosides and properties of 2'-O-alkylated oligoribonucleotides

A general access to 2'-O-alkylated ribonucleosides using the key intermediate 5 is presented. The incorporation of 2'-O-'ethyleneglycol'- and 2'-O-'glycerol'-substituted (i.e., 2'-O-(2-hydroxyethyl)- and 2'-O-(2,3-dihydroxypropyl)-substituted) ribonucleosides into oligonucleotides affords a new generation of oligonucleotides with high affinity for RNA, high specificity, and increased nuclease resistance.

2'-O,5-dimethyluridine: A total synthesis and single crystal X-ray diffraction study

A new method for the synthesis of 2'-O,5-dimethyluridine (5) has provided the title compound in a higher yield. Application of a one-pot ribosylation methodology resulted in an efficient, high yield synthesis of 5-methyluridine (ribothymine, 3b). An X-ray diffraction analysis of 5 disclosed the conformation of the sugar moiety of this nucleoside as anti, N(3'-endo), g+.