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Application of 2,3-aziridino-γ-lactone methodology toward the enantiospecific synthesis of the (3S,4S)-isomer of dihydroxy-L-glutamic acid

✍ Scribed by Philippe Dauban; Carole de Saint-Fuscien; Robert H Dodd

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
750 KB
Volume
55
Category
Article
ISSN
0040-4020

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Enantiospecific synthesis of 3,4-disubst
Enantiospecific synthesis of 3,4-disubstituted glutamic acids via controlled stepwise ring-opening of 2,3-aziridino-γ-lactone
✍ Zhaohua Yan; Robert Weaving; Philippe Dauban; Robert H. Dodd 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 265 KB

The preparation of enantiomerically pure 3,4-disubstituted glutamic acids is described starting from D-ribose. This preparation involved the use of a 2,3-aziridino-g-lactone whose reactivity towards nucleophiles could be efficiently controlled to allow selective functionalization at the b-position.

First enantiospecific synthesis of a 3,4
First enantiospecific synthesis of a 3,4-dihydroxy-l-glutamic acid [(3S,4S)-DHGA], a new mGluR1 agonist
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AbstractÐThe ®rst synthesis of one of the 4 possible stereoisomers of 3,4-dihydroxy-l-glutamic acid ((3S,4S)-DHGA 3), a natural product of unknown con®guration, is described. The synthesis is based on the Lewis acid catalyzed reaction of benzyl alcohol with a d-ribose-derived 2,3-aziridino-g-lactone