128359-94-4

Upstream product

• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 128388-09-0 (5R,4S,2S)-4-acetoxy-5-hydroxymethyl-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) diester 
• 100-39-0 benzyl bromide 
• 132592-31-5 (5R,4S,2S)-4-acetoxy-5-(hydroxymethyl)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester 
• 129001-50-9 (2S,4S,5RS)-4-acetoxy-5-methoxy-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) diester 
• 129001-59-8 (2S,4S,5RS)-4,5-diacetoxy-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) diester 
• 129001-54-3 (5R,4S,2S)-4-acetoxy-5-<(E)-1-<2(methoxycarbonyl)ethenyl>>-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) diester 
• 132592-30-4 (5R,4S,2S)-4-acetoxy-5-<(E)-1-<2-(methoxycarbonyl)ethenyl>>-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester 
• 129001-51-0 (5RS,4S,2S)-4-acetoxy-5-(phenylseleno)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) diester 
• 128359-95-5 (2S,4S)-Methyl 4-acetoxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 
• 128360-00-9 (2S,4R)-Methyl 4-hydroxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate 
• 51-35-4 4R-4-hydroxyproline 
• 1450984-45-8 (2R,3S)-2-((benzoxycarbonyl)amino)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-yl acetate 

Downstream Products

• 132621-15-9 N-<(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-sulfo-β-D-glucopyranosyl)oxy>-5-(hydroxymethyl)-L-prolyl>-6-aminopenicillinic acid bis(phenylmethyl ester) 
• 132592-38-2 (2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid 1-(phenylmethyl) monoester 
• 132592-37-1 (2S,4S,5R)-4-<(2-acetamido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester 
• 132621-14-8 N-<(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-(hydroxymethyl)-L-prolyl>-6-aminopenicillinic acid bis(phenylmethyl ester) 
• 95975-85-2 bulgecin C 
• 129001-57-6 (2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid bis(phenylmethyl ester) 
• 132592-39-3 (2S,4S,5R)-4-<(2-acetamido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid bis(phenylmethyl ester) 
• 129001-60-1 (2S,4S,5R)-4-((2R,3R,4R,5S,6R)-3-Acetylamino-4-benzyloxy-6-benzyloxymethyl-5-sulfooxy-tetrahydro-pyran-2-yloxy)-5-benzyloxymethyl-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester 
• 129001-55-4 (2S,4S,5R)-5-((benzyloxy)methyl)-4-hydroxy-1,2-pyrrolidinedicarboxylic acid bis-(phenylmethyl ester) 
• 132592-32-6 (5R,4S,2S)-4-hydroxy-5-((phenylmethoxy)methyl)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester 

Relevant academic research and scientific papers

Total Syntheses of Bulgecins A, B, and C and Their Bactericidal Potentiation of the β-Lactam Antibiotics

The bulgecins are iminosaccharide secondary metabolites of the Gram-negative bacterium Paraburkholderia acidophila and inhibitors of lytic transglycosylases of bacterial cell-wall biosynthesis and remodeling. The activities of the bulgecins are intimately

Electrochemical Oxidation of Proline Derivatives: Total Syntheses of Bulgecinine and Bulgecin C

The influence of structure on the efficiency of the electrochemical C-5 oxidation of (2S,4S)-hydroxyproline carbamate esters is presented.Optimum methoxylation was observed with (2S,4S)-4-acetoxy-1,2-pyrrolidine-dicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) ester (19).The corresponding C-5 methoxy derivative 20 was converted into bulgecinine (4) via a stereospecific radical homologation to incorporate the C-5 hydroxymethyl substituent.Bulgecin C (1c) was prepared via a β-stereoselective glycosidation reaction using a 2-azido-2-deoxy-α-D-glucopyranosyl trichloroacetimidate derivative, regiospecific C-4' sulfation, and deprotection.