✦ LIBER ✦
2,3-Dihydroxy-3-{3-[3-(trifluoromethyl)diazirin-3-yl]phenyl}propionic Acid. A Cleavable Carbene-Generating Reagent Used for Photocrosslinking
✍ Scribed by Kogon, Alexander A. ;Bochkariov, Dmitry E. ;Baskunov, Boris P. ;Cheprakov, Andrew V.
- Publisher
- John Wiley and Sons
- Year
- 1992
- Tongue
- English
- Weight
- 342 KB
- Volume
- 1992
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
The synthesis of 2,3‐dihydroxy‐3‐{3‐[3‐(trifluoromethyl)diazirin‐3‐yl]phenyl}propionic acid (8), a new cleavable carbenegenerating reagent used in photocrosslinking experiments in molecular biology is described. This synthesis starts with the bromination of trifluoroacetophenone. The resulting compound 2 is converted into the corresponding diazirine 6 via oxime 3, O‐tosyloxime 4, and diaziridinyl 5 derivatives. The cleavable cis‐diol bond is formed via a cinnamic acid derivative 7 by permanganate oxidation resulting in the title compound 8.