✦ LIBER ✦
Carbapenem antibiotics: Displacement of C-3 sulfur side chain by another thiol moiety, and quaternization of a weaker pyridine nitrogen over a stronger primary amine (preparation of BMY 40732 and BMY 40886)
✍ Scribed by Vanga S. Rao; R. Rémillard; Marcel Ménard
- Publisher
- John Wiley and Sons
- Year
- 1992
- Tongue
- English
- Weight
- 596 KB
- Volume
- 3
- Category
- Article
- ISSN
- 1042-7163
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✦ Synopsis
Abstract
Displacement of sulfoxide moiety by a thiol group is shown to be useful in the preparation of 6‐aminoethyl carbapenem derivatives. Also described is a simple strategy to mask a stronger basic primary amine as a nonbasic, nonnucleophilic imine in order to preferentially alkylate (quaternize) a weaker nitrogen of a pyridine in the same molecule. A discussion on the conformational aspects of the β‐lactam‐opened products is also presented.