1229517-68-3Relevant academic research and scientific papers
Stereoselective synthesis of benzylated prodelphinidins and their diastereomers with use of the mitsunobu reaction in the preparation of their gallocatechin precursors
Krohn, Karsten,Ahmed, Ishtiaq,John, Markus,Letzel, Matthias C.,Kuck, Dietmar
, p. 2544 - 2554 (2010)
The tetrabenzylated catechin 9 was prepared by benzylation of the commercially available pure (+)-catechin (3) and cou-pled with the commercially unavailable pentabenzylated (-)-gallocatechin 10, prepared in a one-step Mitsunobu-type cyclization of the triol 8. The highly stereoselective synthesis of benzylated prodelphinidins - catechin-(4α→8)-gallocate-chin (13), gallocatechin-(4α→8)-gallocatechin (14), and gallo-catechin- (4α→8)-catechin (15) - is reported for the first time. The ESI(+)-CID mass spectra of the coupling products were found to feature regioselective retro-Diels-Alder (RDA) reac-tions and unusual sequential losses of pairs of C7H7' radicals (182 u) from the Na+ adduct ions.
