|
|
| | 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite Basic information |
| Product Name: | 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite | | Synonyms: | 2-Cyanoethoxybis(N,N-diisopropylaMino)phosphine;Bis(diisopropylaMino)(2-cyano;N,N,N',N'-Tetrakis(1-Methylethyl)phosphorodiaMidous Acid 2-Cyanoethyl Ester;2-Cyanoethyl N,N,N',N'-tetra(prop-2-yl)phosphorodiamidoite;2-Cyanoethyl N,N,N',N'-tetrakis(isopropyl)phosphorodiamidite;β-Cyanoethyl-N,N,N`,N`-tertraisopropylphosphorodiaMidite;2-CYANOETHYLTETRAISOPROPYLPHOSPHORO-DIA;2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite 97% | | CAS: | 102691-36-1 | | MF: | C15H32N3OP | | MW: | 301.41 | | EINECS: | 600-337-9 | | Product Categories: | OLED materials,pharm chemical,electronic;Building Blocks;Chemical Synthesis;Organic Building Blocks;Phosphoramidites;Phosphorus Compounds;Phosphorylating and Phosphitylating Agents;Nucleic acids;Regant series;Biochemistry;Nucleosides, Nucleotides & Related Reagents;Phosphorylating and Phosphorothioating Agents;Protecting Agents, Phosphorylating Agents & Condensing Agents;Other | | Mol File: | 102691-36-1.mol |  |
| | 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite Chemical Properties |
| | 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite Usage And Synthesis |
| Description | 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite
is a colorless viscous liquid, which is soluble in most
organic solvents. It is a widely used phosphitylating
reagent for the preparation of various phosphorylated
biomolecules, such as nucleoside carbohydrate
conjugates, phospholipids and glycopeptides. In
particular, this reagent is highly effective for automated
solid-phase DNA/RNA oligonucleotide synthesis. It has shown great utility in the coupling of nucleobases or
carbohydrates via their phosphotriesters in the presence
of activators such as 1H-tetrazole, in moderate yields
under mild conditions.This compound is cheaper
and more stable than 2-cyanoethyl N,N-diisopropylchlorophosphorodiamidite (the other
commonly used phosphinylating reagent)[1]. | | Chemical Properties | Clear to Cloudy Colourless Liquid | | Uses | 2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphordiamidite was used:
- in preparation of prosphoramidite reagent, required for synthesis of 12-mer oligodeoxynucleotide
- as phosphorylating agent in synthesis of 1,2-diacyl-sn-glycerophosphatidylserine
- in situ preparation of deoxyribonucleoside phosphoramidites
- in preparation of 2′-deoxy-2′-fluoro-3′-O-(β-cyanoethyl-N,N-diisopropylphosphoramidic)-5′-O-(4-methoxytrityl)-4′-thio-β-D-arabinouridine and 1-(3-O-(β-cyanoethyl-N,N-diisopropylphosphoramidic)-2-deoxy-2-fluoro-5-O-(4,4′-dimethoxytrityl)-4-thio-β-D-arabinofuranosyl)-thymine
- as reagent for synthesizing phosphitylated nucleotides
| | Uses | Reagent for synthesizing phosphitylated nucleotides.1 | | Application | 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite is an important organic reagent widely used in the preparation of modified and unmodified nucleoside phosphoramidites. Nucleoside phosphoramidites are ideal reagents for polymer-supported synthesis of oligonucleotides. The diisopropylamino leaving group is readily cleaved upon contact with the azole catalyst, resulting in an efficient coupling reaction with the free hydroxyl group on the protected nucleoside. | | Synthesis | 
3-((dichlorophosphaneyl)oxy)propanenitrile could synthesize 2-Cyanoethyl N, N, N', N'-tetraisopropylphosphorodiamidite with diisopropylamine. This method is inexpensive manner using a two-step, one-pot procedure and purified by vacuum distillation[2]. | | References | [1] Hada N, et al. Synthetic studies on glycosphingolipids from Protostomia phyla: syntheses and biological activities of amphoteric glycolipids containing a phosphocholine residue from the earthworm Pheretima hilgendorfi. Carbohydrate Research, 2008; 343: 343, 2221.
[2] Ching S, et al. Synthesis of cyclic di-nucleotidic acids as potential inhibitors targeting
diguanylate cyclase. Bioorganic & Medicinal Chemistry, 2010; 18: 6657-6665. |
| | 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite Preparation Products And Raw materials |
| Raw materials | 5'-AMINO-5'-DEOXYTHYMIDINE-->BIS(DIISOPROPYLAMINO)CHLOROPHOSPHINE-->2-CYANOETHYL PHOSPHORODICHLORIDITE-->Diisopropylamine | | Preparation Products | Ceftibuten-->anionic starch-->DMT-DCYTIDINE (N6-BENZOYL) CYANOETHYL PHOSPHORAMIDITE)-->DMT-dG(dmf) Phosphoramidite-->Cytidine, N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-5-(1,7-octadiyn-1-yl)-, 3'-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite]-->Cytidine, N-benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-methyl-, 3'-[2-cyanoethyl bis(1-methylethyl)phosphoramidite], (S)- (9CI)-->DMT-dA(bz) Phosphoramidite-->3'-DA CEP-->5'-DMT-3'-O-TBDMS-N1-Me-Pseudouricdine-CE-Phosphoramidite-->4-THIO-DU CEP-->(2R,3S,5R)-2-((BIS(4-METHOXYPHENYL)(PHENYL)METHOXY)METHYL)-5-(2,4-DIOXO-5-(3-(2,2,2-TRIFLUOROACETAMIDO)PROP-1-YNYL)-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)TETRAHYDROFURAN-3-YL 2-CYANOETHYL DIISOPROPYLPHOSPHORAMIDITE-->DMT-2'O-Methyl-rU Phosphoramidite |
|