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Synthesis of L-[4,5,5,5-D4]isoleucine: determination of approximate rotamer population about the Cβ-Cγ bond

✍ Scribed by Makoto Oba; Akiko Miyakawa; Masanobu Shionoya; Kozaburo Nishiyama

Book ID: 102371337
Publisher: John Wiley and Sons
Year: 2001
Tongue: French
Weight: 413 KB
Volume: 44
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.439

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✦ Synopsis

Abstract

An asymmetric synthesis of regio‐ and stereoselectively deuterium‐labelled L‐isoleucine was examined. An unsaturated γ‐lactam readily available from L‐pyroglutamic acid was stereoselectively methylated by the Gilman reagent and subsequent oxidation of the hydroxymethyl moiety afforded a 3‐methylpyroglutamate derivative. Introduction of a deuterium atom into the γ‐position was achieved via a radical‐based deuteriation of the corresponding phenyl selenide by tributyltin deuteride. Then, the deuteriated 3‐methylpyroglutamate derivative was converted to L‐[4,5,5,5‐D~4~]isoleucine via a base‐promoted ring opening and a reductive deuteriation of the terminal carboxyl moiety. Copyright © 2001 John Wiley & Sons, Ltd.

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