Synthesis of 3-acylamino-4-hydroxymethyl-2-oxo-1-sulfoazetidines and related compounds.
- 1 January 1984
- journal article
- research article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 32 (4) , 1303-1312
- https://doi.org/10.1248/cpb.32.1303
Abstract
The synthesis of both enantiomers of the trans-3-acylamino-4-hydroxymethyl-2-oxo-1-sulfoazetidines is described. The enantiomers of 4-hydroxymethyl-2-azetidinone were chosen as starting materials, and one was synthesized from L-malic acid. For sulfonation at the N-1 position, the new amidine-N-sulfonic acid was prepared and used. The preparation and antibacterial properties of the 4-acetoxymethyl derivatives are described.This publication has 8 references indexed in Scilit:
- Monobactams. Preparation of (S)-3-amino-2-oxoazetidine-1-sulfonic acids from L-.alpha.-amino-.beta.-hydroxy acids via their hydroxamic estersThe Journal of Organic Chemistry, 1982
- EM5400, a family of monobactam antibiotics produced by Agrobacterium radiobacter. II. Isolation and structure determination.The Journal of Antibiotics, 1982
- SQ 26,180, a novel monobactam. I. Taxonomy, fermentation and biological properties.The Journal of Antibiotics, 1982
- Monocyclic β-lactam antibiotics produced by bacteriaNature, 1981
- Sulfazecin and isosulfazecin, novel β-lactam antibiotics of bacterial originNature, 1981
- Isosulfazecin, a new .BETA.-lactam antibiotic, produced by an acidophilic pseudomonad. Fermentation, isolation and characterization.The Journal of Antibiotics, 1981
- Sulfazecin,a novel .BETA.-lactam antibiotic of bacterial origin. Isolation and chemical characterization.The Journal of Antibiotics, 1981
- The triphenylphosphine-sulfur trioxide adduct as a coupling reagent in peptide synthesisBioorganic Chemistry, 1979