67219-55-0

Usage

Uses

Used in Synthetic Modified DNA and RNA:
5'-O-Dimethoxytrityl-N-benzoyl-desoxycytidine is used as a reactant for the synthesis of modified DNA and RNA, specifically in the site-selective RNA activation by acridine-modified oligodeoxynucleotides in metal-ion catalyzed hydrolysis. This application allows for the development of targeted therapies and diagnostic tools in molecular biology.
Used in Research:
As a research tool, 5'-O-Dimethoxytrityl-N-benzoyl-desoxycytidine is employed in anti-viral and anti-cancer studies. Its unique structure and properties make it a valuable compound for investigating the mechanisms of viral replication and cancer cell growth, potentially leading to the discovery of novel therapeutic agents.
Used in Diels-Alder Reactions:
The 3′-O-(2-cyanoethyl)-N,N-diisopropylphosphoramidite derivatives of 5'-O-Dimethoxytrityl-N-benzoyl-desoxycytidine (DMT-dCBz) are involved in Diels-Alder reactions between diene-modified oligonucleotides and maleimide-derivatized peptides. This application is crucial for the development of new chemical linkages and conjugation strategies in biochemistry and materials science.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C37H35N3O7/c1-44-29-17-13-27(14-18-29)37(26-11-7-4-8-12-26,28-15-19-30(45-2)20-16-28)46-24-32-31(41)23-34(47-32)40-22-21-33(39-36(40)43)38-35(42)25-9-5-3-6-10-25/h3-22,31-32,34,41H,23-24H2,1-2H3,(H,38,39,42,43)

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 4836-13-9 N₄-benzoyl-2'-deoxycytidine 
• 152998-05-5 N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-cytidine 3'-(2-cyanoethylphosphonate) 
• 118352-74-2 5'-O-(4,4'-dimethoxytrityl)-4-N-benzoyl-2'-deoxycytidine-3'-H-phosphonate triethylammonium salt 
• 93-97-0 benzoic acid anhydride 
• 951-77-9 2'-Deoxycytidine 
• 116003-04-4 N₄-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3-O-[O-(2-cyanoethyl)-N,N-(diisopropyl)]phosphoramidite 
• 3992-42-5 2'-deoxycytidine monohydrochloride 
• 31501-22-1 N⁴-benzoyl-1-(3',5'-di-O-benzoyl-2'-deoxy-β-D-ribofuranosyl)-cytosine 
• 98-88-4 benzoyl chloride 
• 3019-98-5 pentachlorophenyl benzoate 
• 1548-84-1 pentafluorophenyl benzoate 
• 65-85-0 benzoic acid 
• 7396-95-4 2,4,5-Trichlorophenyl benzoate 

Downstream Products

• 74405-44-0 5'-O-dimethoxytrityl-N-benzoyldeoxycytidine 3'-succinate 
• 93134-40-8 N⁴-Benzoyl-5'-O-(dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-2'-deoxycytidine 
• 93134-38-4 (2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)tetrahydrofuran-3-yl-4-oxopentanoate 
• 85532-80-5 C₄₈H₅₀N₅O₁₄P 
• 93134-55-5 C₅₂H₅₅N₈O₁₄P 
• 87007-45-2 Phosphoric acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester methyl ester 
• 174523-25-2 N⁴-benzoyl-5'-O-dimethoxytrityl-3'-O-methylthiomethyl-2'-deoxycytidine 
• 91282-69-8 C₄₀H₄₃N₄O₇P 
• 96020-45-0 N⁴-Benzoyl-5'-O-dimethoxytrityl-2'-deoxycytidine-3' 2,5-dichlorophenyl 2-(4-nitrophenyl)-ethyl phosphate 
• 66274-77-9 4-chlorophenyl 5'-O-(4,4'-dimethoxytrityl)-N⁴-benzoyl-2'-deoxycytidin-3'-yl phosphate 
• 84416-78-4 Diethyl-phosphoramidous acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester methyl ester 
• 120942-91-8 Phosphorous acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester bis-(2,2,2-trifluoro-1-trifluoromethyl-ethyl) ester 
• 78635-92-4 Dimethyl-phosphoramidous acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester methyl ester 
• 115147-72-3 C₄₄H₅₁N₄O₇P 

Relevant academic research and scientific papers

A new and convenient approach for the preparation of β-cyanoethyl protected trinucleotide phosphoramidites

Herein we report a convenient approach for the preparation of fully protected trinucleotide synthons to be used for the synthesis of gene libraries. The trinucleotide synthons bear β-cyanoethyl groups at the phosphate residues, and thus can be used in standard oligonucleotide synthesis without additional steps for deprotection and work-up.

Exploring the synthesis of masked phosphoramido 6-vinylcytidine derivatives as building blocks for cross-linking oligonucleotides

In the present work the synthesis of building blocks (2a,b), bearing a masked form of the reactive vinyl group bound to the C-6 position of a cytidine derivative, has been studied. The understanding of byproduct formation together with conformational considerations let us to plan a straightforward approach for the synthesis of the target compounds.

Metallic salt of N4-acylcytidine derivatives, and a method for producing N4-acylcytidine derivatives using the same

The present invention provides a method for producing a high purity N4-acylcytidine derivative. More specially, the invention provides a compound represented by the formula (1): wherein R1 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, or a halogen atom; R2 is a hydrogen atom, an alkoxyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms with a substituent, or a halogen atom; R3 represents a methyl group or a phenyl group; and M represents a positive ion of an alkali metal or an alkaline earth metal, and a compound represented by the formula (2): wherein R1, R2, and R3 are as defined above, produced by using the compound represented by the formula (1).

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 protected 2'-deoxycytidines and hydrated crystals thereof

A protected 2′-deoxycytidine is purified by precipitating the protected 2′-deoxycytidine represented by general formula (3) in the form of a hydrated crystal from a solution containing the protected 2′-deoxycytidine and water, and by recovering the protected 2′-deoxycytidine: wherein R1 represents a 4-methoxytrityl, 4,4′-dimethoxytrityl, or triphenylmethyl group; and B1 represents a cytosine group having a protected amino group. The compound represented by general formula (3) is, in particular, a protected 2′-deoxycytidine represented by formula (4): The 2′-deoxycytidine is used as a raw material for antisense DNA.

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.

Dephosphonylation of protected deoxynucleoside and oligodeoxynucleotide H-phosphonates

The conversion of four 5'-O-(4,4'-dimethoxytrityl)-2'- deoxyribonucleoside 3'-H-phosphonates 1 (B=4, 5, 6 and 7) into their partially-protected nucleoside precursors 3 (B=4, 5, 6 and 7, respectively) in good isolated yields is described. The procedure used is also suitable for the dephosphonylation of protected oligonucleotide H-phosphonate blocks.

A mild and efficient method for the preparation of 5'-dimethoxytrityl- 2'-deoxynucleoside using poly(4-vinylpyridine)costyrene

5'-O-4,4'-Dimethoxytrityl-2'-deoxynucleosides have been synthesized in high yield by the reaction of 2'-deoxynucleosides with 4, 4'-dimethoxytrityl chloride in acetonitrile using poly (4-vinylpyridine)-costyrene(styrene 10%).

Nucleosides and nucleotides. 185. Synthesis and biological activities of 4'α-C-branched-chain sugar pyrimidine nucleosides

A series of 4'α-C-branched-chain pyrimidine nucleosides was synthesized from 2'-deoxycytidine or uridine. In the 2'-deoxycytidine series, the substituent at the 4'α-position affected cytotoxicity against L1210 mouse leukemic cells in vitro in the order Me (23) > CN (22)> C≡CH (21) > CH=CH2 (19) > Et (24) > CH=CHCl (20). However, uridine and cytidine derivatives with ethynyl and cyano groups at the 4'α-position did not show any cytotoxicity. The antiviral activities of these nucleosides against HSV-1, HSV-2, and HIV- 1 in vitro were also examined. Compounds 22 and 23 showed antiviral activities against HSV-1 and HSV-2 without showing significant toxicity to the host cells (MRC-5 cells). Although almost all of the nucleosides showed anti-HIV-1 activities, they were also cytotoxic to the host cells (MT-4).

Nucleoside 5'-methylene phosphonates

Novel oligonucleotides analogs and nucleoside analogs as well as methods for their synthesis are described. The oligonucleotides are useful in diagnostic and therapeutic applications. The oligonucleotides are stable to nuclease degradation.