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Determination of the absolute configuration of (−)‐(3 R )‐ O ‐β‐ D ‐glucopyranosyloxy‐5‐phenylpentanoic acid from Polygonum salicifolium
Author(s) -
Ganci Walter M.,
Kuruüzüm Ayşe,
Çaliş İhsan,
Rüedi Peter
Publication year - 2000
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(2000)12:3<139::aid-chir6>3.0.co;2-3
Subject(s) - chemistry , absolute configuration , enantioselective synthesis , hydrolysis , high performance liquid chromatography , chromatography , absolute (philosophy) , stereochemistry , enzymatic hydrolysis , organic chemistry , catalysis , philosophy , epistemology
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 (3 R )‐hydroxy‐5‐phenylpentanoate by HPLC on Chiralcel® 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. Chirality 12:139–142, 2000. © 2000 Wiley‐Liss, Inc.