Dynamic NMR investigation of two new interconvertible diasteriomeric epimers of natural 2-benzyl-2-hydroxybenzofuranone derivative from Pterocarpus marsupium

The first example of a pair of interconvertible diastereomeric epimers 2α/2β-hydroxy-2- p-hydroxybenzyl-3(2 H)-benzofuranone-7-C-β- d-glucopyranoside isolated from the heartwood of Pterocarpus marsupium is reported. The predominance of 1a over 1b was supported by dynamic exchange rates and activatio...

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Bibliographic Details
Published in:Tetrahedron 2004-02, Vol.60 (9), p.2005-2010
Main Authors: Grover, Rajesh K., Maurya, Rakesh, Roy, Raja
Format: Article
Language:English
Subjects:
Deuterium NMR
Dynamic NMR
Mechanism and Pterocarpus marsupium
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Summary:The first example of a pair of interconvertible diastereomeric epimers 2α/2β-hydroxy-2- p-hydroxybenzyl-3(2 H)-benzofuranone-7-C-β- d-glucopyranoside isolated from the heartwood of Pterocarpus marsupium is reported. The predominance of 1a over 1b was supported by dynamic exchange rates and activation parameters obtained from NMR studies. The mechanism of this unique phenomenon is thought to be operative by the formation of diketone as suggested by deuterium exchange. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.01.012