92973-28-9

Upstream product

• 97764-69-7 (2S,3R)-2-<(benzyloxycarbonyl)amino>-4-(chloroacetoxy)-3-(mesyloxy)butanamide 
• 92973-23-4 (2S,3R)-2-<(benzyloxycarbonyl)amino>-4-(chloroacetoxy)-3-hydroxybutanamide 
• 92754-76-2 (2S,3R)-2-<(benzyloxycarbonyl)amino>-3,4-dihydroxybutanamide 
• 92754-75-1 (2S,3R)-2-<(benzyloxycarbonyl)amino>-3-hydroxy-4-butanolide 
• 117069-23-5 (2S,3R)-2-<(benzyloxycarbonyl)amino>-4-hydroxy-3-(mesyloxy)butanamide 
• 117069-22-4 (2S,3R)-2-<(benzyloxycarbonyl)amino>-3-hydroxy-4-(trimethylsiloxy)butanamide 

Relevant academic research and scientific papers

A Novel Synthesis of the Monobactam Antibiotic Carumonam

A novel synthesis of the monobactam 4, a precursor of the antibiotic carumonam (3), has been achieved via the epoxide methyl (2R,3S)-4-acetoxy-2,3-epoxybutyrate (10).The latter was prepared from calcium L-threonate in three steps and 85percent overall yield.In a related study, ethyl (2R,3S)-4-hydroxy-2,3-epoxybutyrate (17) was prepared from L-(+)-tartaric acid in 45percent overall yield.Treatment of the sodium salt derived from 10 or 17 with ammonia led to a stereo- and regiospecific opening of the oxirane ring to give 20, after esterification, amide formation, and protection of the amino group.Conversion of 20 into 4 was accomplished by selective protection of the primary hydroxy group with chloroacetyl chloride, mesylation, sulfonation with 2-picoline-SO3, and ring closure with potassium bicarbonate.