76054-81-4

Basic information

• Product Name: 3'-O-(4,4'-DIMETHOXYTRITYL)-THYMIDINE
• Synonyms: 3'-O-(4,4'-DIMETHOXYTRITYL)-THYMIDINE
• CAS NO: 76054-81-4
• Molecular Formula: C₃₁H₃₂N₂O₇
• Molecular Weight: 544.59
• Mol File: 76054-81-4.mol

Chemical Properties

• Melting Point: 54-55 °C
• Appearance: /
• Density: 1.34±0.1 g/cm3(Predicted)
• PKA: 9.55±0.10(Predicted)
• CAS DataBase Reference: 3'-O-(4,4'-DIMETHOXYTRITYL)-THYMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-O-(4,4'-DIMETHOXYTRITYL)-THYMIDINE(76054-81-4)
• EPA Substance Registry System: 3'-O-(4,4'-DIMETHOXYTRITYL)-THYMIDINE(76054-81-4)

Safety Data

• Hazardous Substances Data: 76054-81-4(Hazardous Substances Data)

Usage

Uses

3''-O-DMT-thymidine is a hairpin-like oligonucleotides forming G-quadruplexes, They are new aptamers with anti-HIV activity.

Upstream product

• 1228354-90-2 3'-O-(4,4'-diemthoxytrityl)-5'-O-(trimethylacetyl)thymidine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 35898-29-4 5'-benzoylthymidine 
• 199792-87-5 3'-O-(4,4'-dimethoxytrityl)-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]thymidine 
• 164267-52-1 5'-O-tert-butyldimethylsilyl-3'-O-(4,4'-dimethoxytriphenylmethyl)thymidine 
• 86610-76-6 3'-O-(4,4'-dimethoxytrityl)-5'-O-<4,4',4''-tris(benzoyloxy)trityl>thymidine 
• 76054-82-5 5'-O-acetyl-3'-O-dimethoxytrityl-2'-deoxythymidine 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 83866-30-2 3'-O-formyl-2'-deoxythymidine 
• 83866-31-3 5'-O-acetyl-3'-O-formyl-2'-deoxythymidine 
• 35898-31-8 5'-O-acetylthymidine 
• 86610-69-7 5'-O-<4,4',4''-tris(benzoyloxy)trityl>thymidine 
• 96255-87-7 5'-O-<4,4',4''-Tris(levulinoyloxyl)trityl>thymidine 
• 50-89-5 thymidine 

Downstream Products

• 170999-47-0 Di-imidazol-1-yl-phosphinic acid (2R,3S,5R)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 171233-70-8 N⁶-Benzoyl-5'-O-DMTr-2'-deoxyadenosine (3'-5')-3'-O-DMTr-thymidine phosphorfluoridite 
• 174221-86-4 5'-O-dimethoxytrityl-2'-amino-2'-deoxyuridine 
• 177980-15-3 C₆₇H₆₇N₆O₁₉P 
• 351341-22-5 5'-O-(dimethoxytrityl)thymidin-3'-yl 3'-O-(dimethoxytrityl)thymidin-5'-yl H-phosphonothioate 
• 351341-22-5 5'-O-(dimethoxytrityl)thymidin-3'-yl 3'-O-(dimethoxytrityl)thymidin-5'-yl H-phosphonothioate 
• 157793-51-6 3'-O-(4,4'-dimethoxytrityl)thymidin-5'-yl 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl ethyl phosphonate 
• 140839-25-4 3'-O-(4,4'-dimethoxytrityl)thymidine 5'-(hydrogen butanedioate) 

Relevant articles and documents

4′-Epi-DNA: A DNA Mimic Containing 4′-hydroxymethyl-α-l-Xylo-Thymidine with Compact Backbone like RNA

Synthesis of C4′-epi-DNA containing 3′→ 5″ linkages is reported for the first time. Crystal structure study of the monomer indicated that though the dihedral angle O3′-C3′-C4′-C5″ in this case would be like in RNA, the sugar conformation would remain like that in DNA. The study of the effect of this backbone configuration in DNA with respect to its binding to cDNA and RNA is reported in this note.

Synthesis of covalently linked parallel and antiparallel DNA duplexes containing the metal-mediated base pairs T-Hg(ii)-T and C-Ag(i)-C

DNA duplexes fixed in anti-parallel and parallel orientations by introducing covalent linkages have been synthesized and metal ions, Hg(ii) and Ag(i), were incorporated into pyrimidine-pyrimidine base pairs.

A convenient protection for 4-oxopyrimidine moieties in nucleosides by the pivaloyl group

Application of the pivaloyl group as a protection for the N3 position of thymidine and uridine was investigated. Pivaloylation of thymidine is a very rapid reaction proceeding under mild conditions with excellent regioselectivity for sugar or thymine moiety, depending on the amines used. Several pivaloylated thymidine derivatives were obtained by treatment of unprotected thymidine with pivaloyl chloride under various experimental conditions. Stability of the N3-pivaloyl protecting group under basic and acidic conditions was evaluated and the conditions for its selective removal were found.

Novel chemoenzymatic protocol for the synthesis of 3′-O- dimethoxytrityl-2′-deoxynucleoside derivatives as building blocks for oligonucleotide synthesis

An easy, efficient, and scalable chemoenzymatic strategy for the synthesis of 3′-O-dimethoxytrityl-2′-deoxynucleosides has been developed. A key feature of this approach is the regioselective synthesis of 5′-O-levulinyl-2′-deoxynucleosides through enzymatic acylation in the presence of Candida antarctica lipase B. In addition, it was observed that the deblocking of levulinyl group from the 5′-position is perfectly compatible with conventional base protecting groups. To demonstrate the scalability of this method, 3′-O-dimethoxytritylthymidine (4a) was synthesized on 25-g scale. These monomers (4a-d) are useful building blocks for the synthesis of oligonucleotides.

Nucleosidyl-O-methylphosphonates: A pool of monomers for modified oligonucleotides

An unique set of 5′-O- and 3′-O-phosphonomethyl derivatives of four natural 2′-deoxyribonucleosides, 1-(2-deoxy-β-D-threo- pentofuranosyl)thymine, 5′-O- and 2′-O-phosphonomethyl derivatives of 1-(3-deoxy-β-D-erythro-pentofuranosyl)thymine, and 1-(3-deoxy-β-D- threo-pentofuranosyl)thymine has been synthesized as a pool of monomers for the synthesis of modified oligonucleotides. The phosphonate moiety was protected with 4-methoxy-1-oxido-2-pyridylmethyl ester group, serving also as an intramolecular catalyst in the coupling step.

Method for purifying 5' -protected thymidines and novel derivatives thereof

This invention provides a method for efficiently purifying 5′-protected thymidines which cannot be efficiently purified by the prior art. Impurities can be separated by obtaining crystals including a carbonyl-containing solvent to provide a highly pure 5′

Method for purifying 5'-protected thymidines

This invention provides a method for efficiently purifying 5'-protected thymidines which cannot be efficiently purified by the prior art. Impurities can be separated by obtaining crystals including a carbonyl-containing solvent to provide a highly pure 5'

Nucleotides. Part LXV. Synthesis of 2'-Deoxyribonucleoside 5'-Phosphoramidites: New Building Blocks for the Inverse (5'-3')-Oligonucleotide Approach

The syntheses of the 3'-O-(4,4'-dimethoxytrityl)-protected 5'-phosphoramidites 25-28 and 5'-(hydrogen succinates) 29-32, which can be used as monomeric building blocks for the inverse (5'-3')-oligodeoxyribonucleotide synthesis are described (Scheme). These activated nucleosides and nucleotides were obtained by two slightly different four-step syntheses starting with the base-protected nucleosides 13-20. For the protection of the aglycon residues, the well-established 2-(4-nitrophenyl)ethyl (npe) and [2-(4-nitrophenyl)ethoxy]carbonyl (npeoc) groups were used. The assembly of the oligonucleotides required a slightly increased coupling time of 3 min in application of the common protocol (see Table 1). The use of pyridinium hydrochloride as an activator (instead of 1H-tetrazole) resulted in an extremely shorter activation time of 30 seconds. We established the efficiency of this inverse strategy by the synthesis of the oligonucleotide 3'-conjugates 33 and 34 which carry lipophilic caps derived from cholesterol and vitamin E, respectively, as well as by the formation of (3'-3')- and (5'-5')-internucleotide linkages (see Table 2).

A novel approach to oligodeoxyribonucleotides bearing phosphoric acid esters at the 3'-terminals via the phosphoramidite method with allyl protection: An efficient synthesis of base-labile nucleotide-amino acid and - peptide conjugates

A new method for synthesis of 3'-end-phosphorylated DNA oligomers via the phosphoramidite method with allyl protection has been developed. This method is particularly useful for the preparation of derivatives with base- labile structures such as oligoDNA-OPO(OH)OCH2CH(R)Z, in which Z is an electron-withdrawing function. For example, a oligonucleotide-amino acid conjugate, 5'TGTCGACACCCAATT3'-OPO(OH)OCH2CH(NH2)COOH, and a oligonucleotide-peptide conjugate, 5'TGTCGACACCCAATT3'- OPO(OH)OCH2CH(NH2)CONHCH2COOH, have been obtained in high purity.

Synthesis of 3'-azido-3'-deoxythymidine-terminated oligonucleotide

A method of completely chemical synthesis of 3'-azido-3'- deoxythymidine-terminated oligonucleotides via 5'-H-phosphonate of AZT is described.