3-(Diethoxyphosphoryloxy)-1,2,3- benzotriazin-4(3H)-one (DEPBT): A New Coupling Reagent with Remarkable Resistance to Racemization
- 24 May 1999
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 1 (1) , 91-94
- https://doi.org/10.1021/ol990573k
Abstract
The new crystalline phosphate reagent 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT) mediates amide bond formation with a remarkable resistance to racemization. Comparative racemization studies were carried out and DEPBT proved to be superior to typical phosphonium and uronium coupling reagents. DEPBT is easily prepared and is exceedingly stable with a shelf life of months at room temperature. The advantageous properties of DEPBT render it a useful and unique addition to the arsenal of coupling reagents.Keywords
This publication has 13 references indexed in Scilit:
- Solid Phase Synthesis of 3-Acyl-2,4-Pyrrolidinediones (3-Acyl Tetramic Acids) via Mild Cyclative CleavageSynlett, 1998
- Solid-Phase Synthesis of β-SultamsThe Journal of Organic Chemistry, 1997
- Urethane‐protected N‐carboxyanhydrides (UNCAs) as unique reactants for the study of intrinsic racemization tendencies in peptide synthesisChemical Biology & Drug Design, 1997
- A Novel Organophosphorus Compound as a Coupling Reagent for Peptide SynthesisSynthetic Communications, 1996
- Synthesis of large peptides in solutionBiopolymers, 1995
- Coupling N-Methylated Amino Acids Using PyBroP and PyCloP Halogenophosphonium Salts: Mechanism and Fields of ApplicationThe Journal of Organic Chemistry, 1994
- 1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additiveJournal of the American Chemical Society, 1993
- Powerful solvent systems useful for synthesis of sparingly‐soluble peptides in solutionInternational Journal of Peptide and Protein Research, 1992
- L'hexafluorophosphate de O-benzotriazolyl-N,N-tetramethyluronium: Un reactif de couplage peptidique nouveau et efficaceTetrahedron Letters, 1978
- Peptide Coupling Reagents VI1. A Novel, Cheaper Preparation of Benzotriazolyloxytris[dimethylamino]phosphonium Hexafluorophosphate (BOP Reagent)Synthesis, 1976