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(+)-(5R,6S)-2-(1′-Aminoalkyl)-6-(hydroxyalkyl)penem-3-carboxylic Acids

✍ Scribed by Marc Lang; Ernst Hungerbühler; Peter Schneider; Riccardo Scartazzini; Werner Tosch; Edward A. Konopka; Oto Zak

Publisher
John Wiley and Sons
Year
1986
Tongue
German
Weight
220 KB
Volume
69
Category
Article
ISSN
0018-019X

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✦ Synopsis

In continuation of our work on penem antibiotics, novel chiral (5R,6S)-2-(1'-aminoalkyl)-6-(hydroxyalkyl)derivatives 1 have been synthesized by two essentially different strategies. Whereas the starting materials for la-f, azetidinones 2 and 5, were obtained from chiral building blocks (6-aminopenicillanic acid and L-threonine, resp.), the one for lg, azetidinone 9, was derived from racemic 4-acetoxyazetidinone and, as chirai auxiliary, (2R)-2-mercaptopropan-1-01. The 2-aminomethyl derivatives l a (CGP 30779) and If (CGP 31 608) proved the most potent compounds in the antibacterial tests in uitro and showed a well-balanced spectrum of activity by comparison with that of established p-lactams.

') For racemic If, see [l 11

📜 SIMILAR VOLUMES

Synthesis and antibacterial activity of
Synthesis and antibacterial activity of (1′R, 5R, 6R)-2-tert-butyl-6-(1′-hydroxyethyl)penem-3-carboxylic acid
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As with the oxapenems, the 2-tert-butyl substituents substantially increased the hydrolytic stability of penems. The corresponding penems 1 and 2 were prepared and found to be extremely stable compounds. 2 showed good in vitro activity against gram-positive bacteria.

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✍ Dai, Le ;Chen, Fen-Er ;Chen, Min-Qin 📂 Article 📅 2007 🏛 International Union of Crystallography 🌐 English ⚖ 89 KB

The title compound, C 13 H 15 NO 3 , contains a chiral cisdisubstituted oxazine linked to a phenyl ring at the C-2 atom. The racemic crystal structure is stabilized by both intra-and intermolecular C-HÁ Á ÁO hydrogen bonds.