RSS-Feed abonnieren
DOI: 10.1055/s-0029-1219806
2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium Hexafluoro-phosphate (HBTU)
Publikationsverlauf
Publikationsdatum:
15. April 2010 (online)
Introduction
The title compound (HBTU, 1) is a useful condensing agent, which has become in the past decade one of the most popular coupling reagents for in situ activation of peptide synthesis both in solid phase and in solution. [¹-5] The same benzotriazolyl derivative has also been successfully employed for esterifications, as for example in solid-phase nucleotide synthesis. [6] [7] In addition to its high reactivity, HBTU has also been shown to fulfill the very important requirement of minimizing racemization at adjacent sites. Sometimes, hydroxybenzotriazole (HOBt) is used together with HBTU as racemization suppressor. Thus, HBTU effectively performs condensation with high yields and minimal racemization, in simple experimental conditions and within short reaction times.
Figure 1
- 1
Knorr R.Trzeciak A.Bannwarth W.Gillessen D. Tetrahedron Lett. 1989, 30: 1927 - 2
Schreiber JV.Seebach D. Helv. Chim. Acta 2000, 83: 3139 - 3
Ernst T.Richert C. Synlett 2005, 411 - 4
Pon RT.Yu S. Tetrahedron Lett. 1997, 38: 3331 - 5
Gluszok S.Goossens L.Depreux P.Henichart J. Tetrahedron Lett. 2006, 47: 6087 - 6
Pon RT.Yu S.Sanghvi YS. Bioconjugate Chem. 1999, 10: 1051 - 7
Schwope I.Bleczinski CF.Richert C. J. Org. Chem. 1999, 64: 4749 - 8
De Leon-Rodriguez LM.Kovacs Z.Dieckmann GR.Sherry AD. Chem. Eur. J. 2004, 10: 1149 - 9
Liley MJ.Johnson T.Gibson SE. J. Org. Chem. 2006, 71: 1322 - 10
Plant A.Thompson P.Williams DM. J. Org. Chem. 2008, 73: 3714 - 11
Jios JL.Kirin SI.Buceta NN.Weyhermüller T.Della Védova CO.Metzler-Nolte N. J. Organomet. Chem. 2007, 692: 4209 - 12
You S.-L.Kelly JW. Tetrahedron 2005, 61: 241 - 13
Semeraro T.Mugnaini C.Manetti F.Pasquini S.Corelli F. Tetrahedron 2008, 64: 11249