Determination of the absolute configuration of (-)-(3R)-O-beta-D-glucopyranosyloxy-5-phenylpentanoic acid from Polygonum salicifolium

Authors
Ganci, WM Kuruuzum, A Calis, I Ruedi, P
Citation
Wm. Ganci et al., Determination of the absolute configuration of (-)-(3R)-O-beta-D-glucopyranosyloxy-5-phenylpentanoic acid from Polygonum salicifolium, CHIRALITY, 12(3), 2000, pp. 139-142
Citations number
13
Categorie Soggetti
Chemistry & Analysis
Journal title
CHIRALITY
ISSN journal
08990042 → ACNP
Volume
12
Issue
3
Year of publication
2000
Pages
139 - 142
Database
ISI
SICI code
0899-0042(2000)12:3<139:DOTACO>2.0.ZU;2-U
Abstract
The absolute configuration of the title compound has been determined after its enzymatic hydrolysis to 3-hydroxy-5-phenylpentanoic acid, esterificatio n, and identification of the enantiomerically pure methyl (3R)-hydroxy-5-ph enylpentanoate by HPLC on Chiralcel(R)OD-H. For reasons of inconsistent lit erature data, enantioselective reductions of methyl 3-oxo-5-phenylpentanoat e have been reinspected and the stereochemical outcome unequivocally confir med by both chiroptical and HPLC retention data. Chirality 12:139-142, 2000 . (C) 2000 Wiley-Liss, Inc.