93183-15-4

Usage

Uses

Used in Pharmaceutical Industry:
5'-O-(4,4'-DIMETHOXYTRITYL)-N2-ISOBUTYRYL-2'-DEOXYGUANOSINE-3'-(2-CYANOETHYL-N,N-DIISOPROPYL)PHOSPHORAMIDITE is used as a key intermediate in the synthesis of antisense oligonucleotides containing conformationally constrained methoxyaminomethylene, aminooxymethylene, and aminomethylene bridged nucleoside analogs. These modified oligonucleotides have potential applications in the development of novel therapeutic agents for various diseases, including cancer and genetic disorders.
Used in Research and Development:
In the field of research and development, 5'-O-(4,4'-DIMETHOXYTRITYL)-N2-ISOBUTYRYL-2'-DEOXYGUANOSINE-3'-(2-CYANOETHYL-N,N-DIISOPROPYL)PHOSPHORAMIDITE serves as an important building block for the design and synthesis of novel nucleic acid-based molecules with unique properties and functions. These molecules can be used to study the structure, function, and interactions of nucleic acids in biological systems, as well as to develop new tools and techniques for molecular biology and genomics research.

InChI:InChI=1/C10H13N5O4.C7H13N2O3P/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6;1-5(2)7(10)12-13(9)11-6(3)4-8/h3-6,16-17H,1-2H2,(H3,11,13,14,18);5-6H,9H2,1-3H3/t4-,5+,6?;/m0./s1

Upstream product

• 68892-41-1 5'-O-dimethoxytrityl-N-isobutyryldeoxyguanosine 
• 124482-92-4 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine 
• 17425-88-6 N,N-diisopropyl-1,1,1-trimethylsilylamine 
• 108-18-9 diisopropylamine 
• 109-78-4 3-Hydroxypropionitrile 
• 133728-85-5 C₄₇H₆₄N₇O₇P 
• 102691-36-1 N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite 
• 68892-42-2 N-isobutyryl-2'-deoxyguanosine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 7087-68-5 N-ethyl-N,N-diisopropylamine 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 

Downstream Products

• 402920-18-7 C₅₉H₆₂N₉O₁₅P 
• 656249-32-0 C₅₇H₆₄N₁₁O₁₅P 
• 160107-22-2 N₂-isobutyryl-3'-O-(2-cyanoethyl)-phosphonate-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine 
• 863507-30-6 C₅₉H₆₂N₉O₁₅PS 
• 627866-37-9 C₅₄H₆₀N₁₁O₁₄P 
• 1305319-06-5 C₇₇H₉₁N₁₅O₂₀P₂Si 
• 1305318-95-9 C₇₇H₉₁N₁₅O₂₁P₂Si 
• 1305318-96-0 C₇₇H₉₁N₁₅O₂₁P₂Si 
• 1305318-70-0 C₆₀H₇₀N₉O₁₄PSi 

Relevant academic research and scientific papers

ON-DEMAND PHOSPHORAMIDITE SYNTHESIS

The invention relates to a method of synthesis of phosphoramidites by immobilization of a phosphitylation agent on a resin activated to create a charged resin, then putting in contact with the charged resin with a suitable substrate. Phosphoramidites are synthesized in a few minutes from the application of the starting materials. Thus, the process makes it possible to create specific phosphoramidites on demand when they are needed in other applications. The substrates to be applied are mainly nucleosides, thus making it possible to create nucleoside phosphoramidites for the subsequent synthesis of oligonucleotides.

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.

A new and convenient approach for the preparation of β-cyanoethyl protected trinucleotide phosphoramidites

Herein we report a convenient approach for the preparation of fully protected trinucleotide synthons to be used for the synthesis of gene libraries. The trinucleotide synthons bear β-cyanoethyl groups at the phosphate residues, and thus can be used in standard oligonucleotide synthesis without additional steps for deprotection and work-up.

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.

Method of preparing phosphoramidites

Improved methods for preparation of phosphoramidite compounds are disclosed. The phosphoramidites are useful, for example, for the preparation of oligonucleotides by solid state oligonucleotide synthetic regimes.

β-CYANOETHYL N,N-DIALKYLAMINO/N-MORPHOLINOMONOCHLORO PHOSPHOAMIDITES, NEW PHOSPHITYLATING AGENTS FACILITATING EASE OF DEPROTECTION AND WORK-UP OF SYNTHESIZED OLIGONUCLEOTIDES

β-Cyanoethyl monochlorophosphoamidites of the secondary amines N,N-dimethylamine, N,N-diisopropylamine and morpholine have been prepared which showed quantitative phosphitylation of the protected deoxynucleosides.The phosphitylated deoxynucleosides have successfully been used in the formation of internucleotidic bonds. β-Cyanoethyl nucleoside-3'-N,N-diisopropylphosphoamidites have saticfactorily been used for the synthesis of the oligodeoxynucleotide d(CGGTACCG).