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Synthesis, chiral HPLC resolution and configuration assignment of 1-phenylglyceryl trinitrate stereomers

✍ Scribed by Konstantin Chegaev; Loretta Lazzarato; Gian Cesare Tron; Domenica Marabello; Antonella Di Stilo; Clara Cena; Roberta Fruttero; Alberto Gasco; Nicolas Vanthuyne; Christian Roussel

Publisher: John Wiley and Sons
Year: 2006
Tongue: English
Weight: 157 KB
Volume: 18
Category: Article
ISSN: 0899-0042
DOI: 10.1002/chir.20278

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✦ Synopsis

Abstract

As an introductory study of in vitro vasodilating activity, the access to the four stereomers of 1‐phenylglyceryl trinitrate is described using achiral and chiral chromatography. For semi‐preparative separation of the enantiomers, a Chiralcel OD (250 × 10 mm, 10 μm) was used. Catalytic reduction leading to the corresponding stereomers of 1‐phenylglycerol allowed absolute configuration assignments. The same methods were used for the separation and configuration assignment of the enantiomers of 3‐phenylpropane‐1,2‐diyl dinitrate. Chirality, 2006. © 2006 Wiley‐Liss, Inc.

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