118380-84-0

Basic information

• Product Name: N-blocked-5'-O-DMT-2'-O-TBDMS CED cytidine phosphoramidite
• Synonyms: N-blocked-5'-O-DMT-2'-O-TBDMS CED cytidine phosphoramidite;Bz-rC Phosphoramidite;N4-Benzoyl-2'-O-tert-butyldimethylsilyl-5'-O-DMT-cytidine 3'-CE phosphoramidite;Cytidine,N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-[(1,1-dimethylethyl)dimethylsilyl]-,3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite] (9CI);N4-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-tert-butyldimethylsilyl)cytidine 3'-O-[O-(2-cyanoethyl)-N,N'-diisopropylphosphoramidite]
• CAS NO: 118380-84-0
• Molecular Formula: C₅₂H₆₆N₅O₉PSi
• Molecular Weight: 964.179
• EINECS: 2017-001-1
• Mol File: 118380-84-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• PKA: 8.55±0.20(Predicted)
• CAS DataBase Reference: N-blocked-5'-O-DMT-2'-O-TBDMS CED cytidine phosphoramidite(CAS DataBase Reference)
• NIST Chemistry Reference: N-blocked-5'-O-DMT-2'-O-TBDMS CED cytidine phosphoramidite(118380-84-0)
• EPA Substance Registry System: N-blocked-5'-O-DMT-2'-O-TBDMS CED cytidine phosphoramidite(118380-84-0)

Safety Data

• Hazardous Substances Data: 118380-84-0(Hazardous Substances Data)

Usage

Uses

Used in Molecular Biology Applications:
N-blocked-5'-O-DMT-2'-O-TBDMS CED cytidine phosphoramidite is used as a building block for the synthesis of oligonucleotides for various molecular biology applications. The protecting groups in the compound allow for precise control of the synthesis process, ensuring the correct formation of phosphodiester bonds and the desired sequence of the oligonucleotide.
Used in Solid-Phase Synthesis:
In the solid-phase synthesis industry, N-blocked-5'-O-DMT-2'-O-TBDMS CED cytidine phosphoramidite is used as a key component for the assembly of oligonucleotides. The protecting groups facilitate the stepwise addition of nucleotides to the growing chain, enabling the synthesis of oligonucleotides with high accuracy and yield.
Used in Research and Development:
In the research and development sector, N-blocked-5'-O-DMT-2'-O-TBDMS CED cytidine phosphoramidite is utilized for the design and synthesis of novel oligonucleotides with specific properties and functions. N-blocked-5'-O-DMT-2'-O-TBDMS CED cytidine phosphoramidite's protecting groups allow researchers to explore various modifications and applications of oligonucleotides in areas such as drug discovery, diagnostics, and therapeutics.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-blocked-5'-O-DMT-2'-O-TBDMS CED cytidine phosphoramidite is employed as a crucial component in the development of antisense drugs, RNA interference (RNAi) therapies, and other nucleic acid-based therapeutics. N-blocked-5'-O-DMT-2'-O-TBDMS CED cytidine phosphoramidite's protecting groups enable the synthesis of highly specific and potent oligonucleotides that can modulate gene expression and target disease-causing genes.
Used in Diagnostics:
In the diagnostics field, N-blocked-5'-O-DMT-2'-O-TBDMS CED cytidine phosphoramidite is used for the synthesis of oligonucleotide probes and primers for various molecular diagnostic techniques, such as polymerase chain reaction (PCR), DNA sequencing, and microarrays. The protecting groups ensure the accurate and reliable synthesis of these probes and primers, contributing to the sensitivity and specificity of diagnostic assays.

Upstream product

• 129666-74-6 5’-O-(1,1-bis(4-methoxyphenyl)-1-phenylmethyl)-2’-O-tert-butyldimethylsilylcytidine 
• 102691-36-1 N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite 
• 124482-92-4 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine 

Downstream Products

• 1134195-54-2 C₆₁H₇₇N₆O₁₆PSi₂ 
• 118362-05-3 C₄₆H₅₈N₅O₁₄PSi*H₃N 

Relevant articles and documents

Methods of producing phosphitylated compounds

Provided are methods of producing phosphitylated compounds, including 3′-O-phosphoramidites, comprising the step of reacting a hydroxyl-containing compound with a phosphitylating agent in the presence of a phosphitylation activator selected from the group consisting of: (1) acid-base complexes derived from an amine base of Formula I 1wherein R, R1, and R2 are independently C1-C10 alkyl, C1-C10 cycloalkyl, C1-C10 aryl, C1-C10 aralkyl, C1-C10 heteroalkyl, or C1-C10 heteroaryl; (2) acid-base complexes derived from an amine base of Formula II 2wherein R3, R4, R5, R6, and R7 are independently hydrogen, C1-C10 alkyl, C1-C10 cycloalkyl, C1-C10 aryl, C1-C10 aralkyl, C1-C10 heteroalkyl, or C1-C10 heteroaryl, and at least one of R3, R4, R5 R6, and R7 is not hydrogen.; (3) acid-base complexes derived from a diazabicyclo amine base; (4) zwitterionic amine complexes; and (5) combinations of two or more thereof, to produce a phosphitylated compound.

New Nucleoside Phosphoramidites and Coupling Protocols for Solid-Phase RNA Synthesis

The 5'-O-(4,4'-dimethoxytrityl)-2'-O-(trialkylsilyl)ribonucleoside 3'-O-(2-cyanoethyl N,N-diethylphosphoramidites) 3, 5, 7, and 9, modified monomers for RNA synthesis, were prepared from 2-cyanoethyl N,N-diethylchlorophosphoramidite (1).In conjunction with newly developed coupling protocols for automated solid-phase synthesis, they afforded synthetic oligoribonucleotides up to 74 base units in length.The performance of the new compounds was compared to the analogous 5'-O-(4,4'-dimethoxytrityl)-2'-O-(trialkylsilyl)ribonucleoside 3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidites) 4, 6, 8, and 10.Complete removal of benzoyl groups from N2-benzoylguanosine, which was incorporated into some of the synthetic oligoribonucleotides, was demonstrated.Purification procedures by reverse phase HPLC and PAGE methods are also presented.

Some Steric Aspects of Synthesis of Oligoribonucleotides by Phosphoramidite Approach on Solid Support

The influence of 2'-O-substituents (i.e. methyl, tetrahydropyranyl, tert-butyldimethylsilyl) on the chemical synthesis of oligoribonucleotides by phosphoramidite approach on solid support is described and compared with respective 2'-deoxynucleoside derivative.The observations on reactivity of these different 2'-O-protected derivatives at phosphatilation and condensation steps show their strong hindrance dependence.Some other aspects like reactivity of tetrahydropyranyl diastereoisomers, 3'- and 2'-O-phosphoramidites and some chemical properties of 2'-O-(tert-butyldimethylsilyl) protecting group are also presented.