2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite

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

The Uses of 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite

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

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.