154110-40-4

Basic information

• Product Name: (2R,3S,5R)-5-(4-ACETAMIDO-2-OXOPYRIMIDIN-1(2H)-YL)-2-((BIS(4-METHOXYPHENYL)(PHENYL)METHOXY)METHYL)TETRAHYDROFURAN-3-YL 2-CYANOETHYL DIISOPROPYLPHOSPHORAMIDITE
• Synonyms: (2R,3S,5R)-5-(4-ACETAMIDO-2-OXOPYRIMIDIN-1(2H)-YL)-2-((BIS(4-METHOXYPHENYL)(PHENYL)METHOXY)METHYL)TETRAHYDROFURAN-3-YL 2-CYANOETHYL DIISOPROPYLPHOSPHORAMIDITE;Ac-dC Phosphoramidite;(2R,3S,5R)-5-(4-acetamido-2-oxopyrimidin-1(2H)-YL)-2-((BIS(4-methoxyphenyl)(phenyl)methoxy)methyl)tetrahydrofuran-3-YL 2-cyanoethy diisopropylphosphoramidite;N-Acetyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-3'-[2-cyanoethyl-N,N-bis(1-methylethyl)phosphoramidite]cytidine;N4-Acetyl-2'-deoxy-5'-O-DMT-cytidine 3'-Me phosphonamidite;N4-Acetyl-2'-deoxy-5'-O-DMT-cytidine 3'-CE phosphoramidite;N4-Acetyl-2'-deoxy-3'-O-DMT-cytidine 5'-CE phosphoramidite;(2S,3R,5S)-5-(4-AcetaMido-2-oxopyriMidin-1(2H)-yl)-2-((bis(4-Methoxyphenyl)(phenyl)Methoxy)Methyl)tetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoraMidite
• CAS NO: 154110-40-4
• Molecular Formula: C₄₁H₅₀N₅O₈P
• Molecular Weight: 771.86
• EINECS: 2017-001-1
• Mol File: 154110-40-4.mol
• Article Data: 2

Chemical Properties

• Appearance: white to off-white/
• Storage Temp.: ?20°C
• PKA: 10.26±0.20(Predicted)
• CAS DataBase Reference: (2R,3S,5R)-5-(4-ACETAMIDO-2-OXOPYRIMIDIN-1(2H)-YL)-2-((BIS(4-METHOXYPHENYL)(PHENYL)METHOXY)METHYL)TETRAHYDROFURAN-3-YL 2-CYANOETHYL DIISOPROPYLPHOSPHORAMIDITE(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,5R)-5-(4-ACETAMIDO-2-OXOPYRIMIDIN-1(2H)-YL)-2-((BIS(4-METHOXYPHENYL)(PHENYL)METHOXY)METHYL)TETRAHYDROFURAN-3-YL 2-CYANOETHYL DIISOPROPYLPHOSPHORAMIDITE(154110-40-4)
• EPA Substance Registry System: (2R,3S,5R)-5-(4-ACETAMIDO-2-OXOPYRIMIDIN-1(2H)-YL)-2-((BIS(4-METHOXYPHENYL)(PHENYL)METHOXY)METHYL)TETRAHYDROFURAN-3-YL 2-CYANOETHYL DIISOPROPYLPHOSPHORAMIDITE(154110-40-4)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 154110-40-4(Hazardous Substances Data)

Usage

Uses

Ac-dC phosphoramidite is a nucleoside used in the preparation of cytidine-?based nucleotide-?lipids which can act as supramolecular gelators depending on both the nucleobase and the presence of salts.

Upstream product

• 951-77-9 2'-Deoxycytidine 
• 124482-92-4 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine 
• 100898-63-3 5’-O-(4,4’dimethoxytrityl)-N4-(acetyl)-2'-deoxycytidine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 32909-05-0 N⁴-acetyl-2'-deoxycytidine 

Downstream Products

• 1422956-11-3 (2R,3S,5R)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl((2R,3S,4R,5R)-4-azido-5-(6-benzamido-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl)methyl 2-cyanoethyl phosphate 
• 140613-57-6 5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-O-[(2-cyanoethyl)-N,N-diisopropylphosphoramidite] 

Relevant articles and documents

Ultrafast cleavage and deprotection of oligonucleotides synthesis and use of C(Ac) derivatives

We have investigated the use of alkylamines as fast cleavage and deprotection reagents for the solid phase synthesis of oligonucleotides and found methylamine/ammonium hydroxide (or methylamine) as an efficient reagent. The transamination side product formed with the commonly used dC(b2) has been eliminated by the use of dC(Ac) phosphoramidite. This system has successfully been used in the synthesis of oligonucleotides and oligonucleoside phosphorothioates. DMT dC(Ac) hydrogen phosphonate and DMT ribo C(Ac)-2'-OMe phosphoramidite also have been prepared and used in the synthesis of oligonucleotides.