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
• Article Data: 3

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

General Description

N-blocked-5'-O-DMT-2'-O-TBDMS CED cytidine phosphoramidite is a type of modified cytidine phosphoramidite used in the synthesis of oligonucleotides. The compound is N-blocked, meaning that the nitrogen atom in the cytidine base is protected, and it also contains a 5'-O-DMT protecting group on the sugar moiety and a 2'-O-TBDMS protecting group on the 2'-hydroxyl group of the ribose ring. This phosphoramidite is commonly utilized in solid-phase 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.

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.

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.