A reagent commonly used in the synthesis of peptides. A very efficient reagent that allows in situ formation of hydroxybenzotriazolyl esters 1. Its main disadvantage is that the highly toxic and carcinogenic HMPA is formed during the course of the reaction 2,3. BOP allows the efficient in situ traping of the dipeptide amine by the acylating reagent. This specific ability of BOP for avoiding diketopiperazine formation is illustrated in liquid phase synthesis as well as in the SPPS 4. BOP is also used as a condensing agent to promote internucleotidic bond formation in phosphotriester oligodeoxyribonucleotide synthesis 5,6. A useful coupling agent to synthesis nitriles from aldoximes 7.
1. Tetrahedron Lett. 1996, 37, 4237.
2. Tetrahedron Lett. 1994, 35, 5603.
3. Ukr. Bio. Acta 2005, 2, 13.
4. Tetrahedron Lett. 1990, 31, 7363.
5. Eur. J. Org. Chem. 2008, 10, 1705.
6. Ukr. Bio. Acta 2004, 1, 23.
7. J. Org. Chem. 2009, 74, 3079.