121058-82-0

Basic information

• Product Name: 5'-O-(4,4'-Dimethoxytrityl)-N4-acetyl-2'-deoxycytidine
• Synonyms: N4-ACETYL-5'-(DIMETHOXYTRITYL)-2'-DEOXYCYTIDINE;N-ACETYL-5'-DMT DEOXYCYTIDINE;DMT-NAC-DC;5'-O-(4,4'-DIMETHOXYTRITYL)-N4-ACETYL-2'-DEOXYCYTIDINE;DTN-003 5'-O-(4,4'-DiMethoxytrityl)-N4-Acetyl-2'-Deoxycytidine;5'-O-(4,4'-DiMethoxytrityl)-N4-acetyl cytidine;Cytidine, N-acetyl-5'-O-[bis(4-Methoxyphenyl)phenylMethyl]-;5'-O-DMT-N4-Ac cytidine
• CAS NO: 121058-82-0
• Molecular Formula: C₃₂H₃₃N₃O₈
• Molecular Weight: 571.62
• Mol File: 121058-82-0.mol

Chemical Properties

• Appearance: /
• Density: 1.32±0.1 g/cm3(Predicted)
• PKA: 10.21±0.20(Predicted)
• CAS DataBase Reference: 5'-O-(4,4'-Dimethoxytrityl)-N4-acetyl-2'-deoxycytidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-(4,4'-Dimethoxytrityl)-N4-acetyl-2'-deoxycytidine(121058-82-0)
• EPA Substance Registry System: 5'-O-(4,4'-Dimethoxytrityl)-N4-acetyl-2'-deoxycytidine(121058-82-0)

Safety Data

• Hazardous Substances Data: 121058-82-0(Hazardous Substances Data)

Usage

Uses

Used in Oligonucleotide Synthesis:
5'-O-(4,4'-Dimethoxytrityl)-N4-acetyl-2'-deoxycytidine is used as a protected nucleoside for the synthesis of oligonucleotides. The reason for its use is to facilitate the selective attachment to a controlled pore glass (CPG) support, which is crucial for the controlled and accurate assembly of DNA sequences.
Used in DNA Synthesis:
In the DNA synthesis industry, 5'-O-(4,4'-Dimethoxytrityl)-N4-acetyl-2'-deoxycytidine is used as a key component in the creation of custom DNA oligos. Its role is to ensure the protection of the amine group on the cytosine molecule, which is vital for the successful synthesis of the desired DNA sequences.
Used in Biological Research Applications:
5'-O-(4,4'-Dimethoxytrityl)-N4-acetyl-2'-deoxycytidine is used as a protected nucleoside in various biological research applications. Its purpose is to provide a stable and controlled environment for the synthesis of DNA oligos, which are essential for studying genetic information, gene expression, and other molecular biology processes.

Upstream product

• 51432-41-8 O^2'_,O3'_,O5'-tris-trimethylsilanyl-cytidine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 3768-18-1 N-acetylcytidine 
• 65-46-3 CYTIDINE 
• 108-24-7 acetic anhydride 

Downstream Products

• 231957-28-1 N-{1-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(2-nitro-benzyloxymethoxy)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-acetamide 
• 1146634-30-1 C₃₈H₄₃N₃O₁₀ 
• 1097131-01-5 N₄-acetyl-2'-O-pivaloyloxymethyl-5'-O-(4,4'-dimethoxytrityl)cytidine 
• 863408-42-8 N⁴-acetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-(2-cyanoethoxymethyl)cytidine 
• 121058-88-6 (2R,3R,4R,5R)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-2-((bis(4-methoxyphenyl)(phenyl)met hoxy)methyl)-4-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-3-yl(2-cyanoethyl)diisopropylphosphoramidite 
• 121058-85-3 5'-O-DMTr-2'-O-TBDMS-N4-acetylcytidine 
• 1053267-56-3 {1-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(2-nitro-benzyloxymethoxy)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-carbamic acid 2-nitro-benzyl ester 
• 149622-84-4 4-Amino-1-[(2R,3R,4R,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(2-nitro-benzyloxymethoxy)-tetrahydro-furan-2-yl]-1H-pyrimidin-2-one 
• 289891-54-9 N⁴-acetyl-2'-O-[(3-bromopropoxy)methyl]-5'-O-(4,4'-dimethoxytrityl)cytidine 3'-(2-cyanoethyl diisopropylphosphoramidite) 
• 5040-18-6 4-N-2',3',5'-O-tetraacetylcytidine 
• 253586-12-8 N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropyl)silyloxy]methyl}cytidine 3'-(2-cyanoethyl diisopropylphosphoramidite) 
• 863408-47-3 N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-cyanoethoxymethyl)cytidine 3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite) 

Relevant articles and documents

Methylamine Deprotection Provides Increased Yield of Oligoribonucleotides

Use of methylamine or methylamine/ammonium hydroxide as a cleavage and deprotection reagent for the solid phase synthesis of oligoribonucleotides has significantly increased the yield of the full length oligoribonucleotides as compared to the use of conventional ammonium hydroxide/ethanol.

UNA (unlocked nucleic acid): A flexible RNA mimic that allows engineering of nucleic acid duplex stability

UNA (unlocked nucleic acid) monomers are acyclic derivatives of RNA lacking the C2′-C3′-bond of the ribose ring of RNA. Synthesis of phosphoramidite UNA building blocks of the nucleobases adenine, cytosine, guanine, and uracil is described herein together

A base-labile group for 2′-OH protection of ribonucleosides: A major challenge for RNA synthesis

A base-labile group for 2'-OH protection of ribonucleosides was investigated. The solid support was dried by blowing argon through a DNA synthesizer and was first treated with 10% anhydrous piperidine in CH 3CN at room temperature for 15 minutes to eliminate cyanoethyl groups from phosphates. The piperidine solution was removed from the column and the solid support was washed with CH3CN. The three ammoniacal eluates were collected in a screw-capped glass vial and were left at room temperature for a further 1.5 hours to completely deprotect nucleobases and 2'-hydroxyl groups. The fully deprotected oligonucleotide was transferred to a 50 mL round-bottomed flask and isopropylamine was added to the solution before evaporation to dryness. It was observed that PivOM method provides highly pure RNA without any additional desalting step.

A new RNA synthetic method with a 2′-O-(2-cyanoethoxymethyl) protecting group

(Chemical Equation Presented) A novel method for the synthesis of RNA oligomers with 2-cyanoethoxymethyl (CEM) as the 2′-hydroxyl protecting group has been developed. The new method allows the synthesis of oligoribonucleotides with an efficiency and final

Reliable chemical synthesis of oligoribonucleotides (RNA) with 2′-O-[(triisopropylsilyl)oxy]methyl(2′-O-tom)-protected phosphoramidites

A method for the introduction of the 2′-O-[(triisopropylsilyl)oxy]methyl (=tom) group into N-acetylated, 5′-O-dimethoxytritylated ribonucleosides is presented. The corresponding 2′-O-tom-protected phosphoramidite building blocks were obtained in pure form and were successfully employed for the routine synthesis of oligoribonucleotides on DNA synthesizers. Under DNA coupling conditions (2.5 min coupling time for a 1.5-μmol synthesis scale) and with 5-(benzylthio)-1H-tetrazole (BTT) as activator, 2′-O-tom-protected phosphoramidites exhibited average coupling yields >99.4%. The combination of N-acetyl and 2′-O-tom protecting groups allowed a reliable and complete two-step deprotection, first with MeNH2 in EtOH/H2O and then with Bu4NF in THF, without concomitant destruction of the product RNA sequences.

Synthesis of a new transition-state analog of the sialyl donor. Inhibition of sialyltransferases

A new class of glycosyltransferase inhibitor has been designed and synthesized. The designed inhibitors 3a/3b provide conformational mimicry of the transition state in sialyltransfer reactions. The key synthetic steps involve a Meinwald rearrangement and a palladium-catalyzed carbonylation reaction. The results of kinetic studies show that 3a/3b exhibit significant inhibition on both 2,3- and 2,6-sialytransferases.

The synthesis of allyl- and allyloxycarbonyl-protected RNA phosphoramidites. Useful reagents for solid-phase synthesis of RNAs with base-labile modifications

The synthesis of allyl- and allyloxycarbonyl (AOC)-protected RNA phosphoramidites is reported. The use of allyl and AOC groups allows the chemistry of solid-phase RNA synthesis to be expanded to include base-labile modified nucleosides, such as acetylcytidine. The allyl- and AOC-protective chemistry can be further expanded for the construction of RNAs on solid supports and affinity columns.

THE USE OF LABILE BASE PROTECTING GROUPS IN OLIGORIBONUCLEOTIDE SYNTHESIS

The use of phenoxyacetyl group for the protection of the exocyclic amino function of purine bases and acetyl group for cytosine in oligonucleotide synthesis by the cyanoethylphosphoramidite approach is described.A side reaction - i.e. partial replacement of phenoxyacetyl group of protected guanines by acetyl group - was observed during the capping step.It can be avoided by the use of phenoxyacetic anhydride in place of acetic anhydride.