RSS-Feed abonnieren
DOI: 10.1055/s-0032-1317955
2-Cyanoethyl N,N,N′,N′-Tetraisopropylphosphorodiamidite
Publikationsverlauf
Publikationsdatum:
19. Dezember 2012 (online)
Introduction
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.[ 1 ] In particular, this reagent is highly effective for automated solid-phase DNA/RNA oligonucleotide synthesis.[ 2 ]
2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphorodiamidite 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.[1] [2] Additionally, 2-cyanoethyl N,N,N′,N′-tetraisopropylphosphorodiamidite is cheaper and more stable than 2-cyanoethyl N,N-diisopropylchlorophosphorodiamidite, the other commonly used phosphinylating reagent.[ 3 ]
2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphorodiamidite is commercially available but can also be prepared in an inexpensive manner using a two-step, one-pot procedure and purified by vacuum distillation (Scheme [1]).[ 4 ]
-
References
- 1a Anraku K, Inoue T, Sugimoto K, Kudo K, Okamoto Y, Morii T, Mori Y, Otsuka M. Bioorg. Med. Chem. 2011; 19: 6833
- 1b Hada N, Shida Y, Shimamura H, Sonoda Y, Kasahara T, Sugita M, Takeda T. Carbohydr. Res. 2008; 343: 2221
- 1c Steven V, Graham D. Org. Biomol. Chem. 2008; 6: 3781
- 2a Hentschel S, Alzeer J, Angelov T, Scharer OD, Luedtke NW. Angew. Chem. Int. Ed. 2012; 51: 3466
- 2b Münzel M, Lischke U, Stathis D, Pfaffeneder T, Gnerlich FA, Deiml CA, Koch SC, Karaghiosoff K, Carell T. Chem.–Eur. J. 2011; 17: 13782
- 2c Seio K, Kurohagi S, Kodama E, Masaki Y, Tsunoda H, Ohkubo A, Sekine M. Org. Biomol. Chem. 2012; 10: 994
- 3a Pedersen DS, Rosenbohm C, Koch T. Synthesis 2002; 802
- 3b Sanghvi YS, Guo ZQ, Pfundheller HM, Converso A. Org. Process Res. Dev. 2000; 4: 175
- 4 Ching SM, Tan WJ, Chua KL, Lam Y. Bioorg. Med. Chem. 2010; 18: 6657
- 5 Sheppard TL, Wong C.-H, Joyce GF. Angew. Chem. Int. Ed. 2000; 39: 3660
- 6 Yamada T, Okaniwa N, Saneyoshi H, Ohkubo A, Seio K, Nagata T, Aoki Y, Takeda S.-i, Sekine M. J. Org. Chem. 2011; 76: 3042
- 7 Lin J, He K, Ramsay Shaw B. Helv. Chim. Acta 2000; 83: 1392
- 8 Smith JM, Borsenberger V, Raftery J, Sutherland JD. Chem. Biodiv. 2004; 1: 1418
- 9 Nishida Y, Takamori Y, Matsuda K, Ohrui H, Yamada T, Kobayashi K. J. Carbohydr. Chem. 1999; 18: 985
- 10 Rodríguez-Pérez T, Fernández S, Sanghvi YS, Detorio M, Schinazi RF, Gotor V, Ferrero M. Bioconjugate Chem. 2010; 21: 2239