121058-88-6

Basic information

• Product Name: N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]cytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite
• Synonyms: 2’-TBDMS-rC(N-Ac) Phosphoramidite;5'-O-DMT-2'-TBDMS-rC(N-Ac)-3'-CEDPA;N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]cytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite;(2R,3R,4R,5R)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-(tert-butyldimethylsilyloxy)tetrahydrofuran-3-yl 2-cyanoethyl diisopropylphosphoramidite;REF DUPL: 2'-TBDMS-rC(N-ac) Phosphoramidite;Ac-rC Phosphoramidite;N4-Acetyl-2'-O-tert-butyldimethylsilyl-5'-O-DMT-cytidine 3'-CE phosphoramidite;(2S,3S,4S,5S)-5-(4-AcetaMido-2-oxopyriMidin-1(2H)-yl)-2-((bis(4-Methoxyphenyl)(phenyl)Methoxy)Methyl)-4-((tert-butyldiMethylsilyl)oxy)tetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoraMidite
• CAS NO: 121058-88-6
• Molecular Formula: C₄₇H₆₄N₅O₉PSi
• Molecular Weight: 902.1
• EINECS: 2017-001-1
• Mol File: 121058-88-6.mol
• Article Data: 5

Chemical Properties

• Appearance: white to off-white/
• Storage Temp.: ?20°C
• PKA: 10.16±0.20(Predicted)
• CAS DataBase Reference: N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]cytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]cytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite(121058-88-6)
• EPA Substance Registry System: N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]cytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite(121058-88-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 121058-88-6(Hazardous Substances Data)

Usage

Uses

DMT-2′O-TBDMS-rC(ac) Phosphoramidite was used for inverse electron-demand Diels-Alder reactions for selective and efficient labeling of RNA.

Upstream product

• 124482-92-4 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine 
• 121058-85-3 5'-O-DMTr-2'-O-TBDMS-N4-acetylcytidine 
• 121058-82-0 N⁴-acetyl-5'-O-(4,4'-dimethoxytrityl)cytidine 
• 102691-36-1 N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite 
• 65-46-3 CYTIDINE 
• 51432-41-8 O^2'_,O3'_,O5'-tris-trimethylsilanyl-cytidine 
• 3768-18-1 N-acetylcytidine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 121058-85-3 5'-O-DMTr-2'-O-TBDMS-N4-acetylcytidine 
• 1174673-48-3 C₆₂H₈₀N₁₃O₁₂PSi 
• 897626-57-2 C₄₅H₆₂N₅O₈PSi 

Relevant articles and documents

Microwave-assisted preparation of nucleoside-phosphoramidites

Microwave-assisted phosphitylation of sterically hindered nucleosides is demonstrated to be an efficient method for the preparation of corresponding phosphoramidites (otherwise onerous under standard conditions) and is shown to be general in its applicability. the Partner Organisations 2014.

Methods for synthesizing nucleosides, nucleoside derivatives and non-nucleoside derivatives

The present invention provides methods for the chemical synthesis of nucleosides and derivatives thereof, including 2′-amino, 2′-N-phthaloyl, 2′-O-methyl, 2′-O-silyl, 2′OH nucleosides, C-nucleosides, nucleoside phosphoramidites, C-nucleoside phosphoramidites, and non-nucleoside derivatives.

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.