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Bis(4-nitrophenyl) carbonate is used as a reagent for preparation of symmetrical and unsymmetrical urea and 4-nitrophenyl esters of N-protected amino acids. It acts as a peptide coupling reagent. It finds application as a reagent for the preparation of carbamate linked cytosines.
Reagent for peptide coupling in the presence of triethylamine in DMF, via the p-nitrophenyl active ester: Liebigs Ann. Chem., 655, 189 (1962); Helv. Chim. Acta, 46, 795 (1963). See Appendix 6.
Has also been used as a coupling reagent in the synthesis of carbamate linked cytosine oligomers: J. Org. Chem., 52, 4202 (1987), and of ureido sugars: Carbohydr. Res., 203, 302 (1990).
Castro, E. A.; Aliaga, M. E.; Gazitua, M.; Pavez, P.; Santos, J. G. Kinetics and mechanism of the aminolysis of bis(4-nitrophenyl) carbonate and O-(4-nitropheny) S-(4-nitrophenyl) thio and dithiocarbonate. J. Phys. Org. Chem. 2014, 27 (4), 265-268.
Li, J.; Gerlach, R. L.; Jonsson, C. B.; Gray, B. D.; Pak, K. Y.; Ng, C. K. Characterization of (18)F-dipicolylamine (DPA) derivatives in cells infected with influenza virus. Nucl. Med. Biol. 2015, 42 (3), 283-291.
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