Determination of the absolute configuration of (-)-(3R)-O-beta-D-glucopyranosyloxy-5-phenylpentanoic acid from Polygonum salicifolium.
The absolute configuration of the title compound has been determined after its enzymatic hydrolysis to 3-hydroxy-5-phenylpentanoic acid, esterification, and identification of the enantiomerically pure methyl (3R)-hydroxy-5-phenylpentanoate by HPLC on Chiralcel(R)OD-H. For reasons of inconsistent literature data, enantioselective reductions of methyl 3-oxo-5-phenylpentanoate have been reinspected and the stereochemical outcome unequivocally confirmed by both chiroptical and HPLC retention data.
Ganci
W M
WM
University of Zurich, Institute of Organic Chemistry, Zürich, Switzerland.
Kuruüzüm
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A
Caliş
I
I
Rüedi
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P
D002851:Chromatography, High Pressure Liquid; D005960:Glucosides / Q000737:chemistry*; D019664:Polygonaceae / Q000737:chemistry*; D013237:Stereoisomerism
D005960:Glucosides; C406347:glucopyranosyloxy-5-phenylpentanoic acid