228267-27-4

Upstream product

• 72496-37-8 ((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-acetaldehyde 
• 87736-74-1 4-(tert-butyldimethylsiloxymethyl)bromobenzene 

Downstream Products

• 228267-30-9 (3 R)-N-allyloxycarbonyl-1-(4-hydroxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutylamine 
• 262845-98-7 (1R,3R)-N-allyloxycarbonyl-1-(4-azidomethylphenyl)-4-tert-butyldimethylsiloxy-3-hydroxybutylamine 
• 262846-34-4 (1S,3R)-N-allyloxycarbonyl-1-(4-azidomethylphenyl)-4-tert-butyldimethylsiloxy-3-hydroxybutylamine 
• 170587-06-1 (2S,4S)-4-acetylthio-2-[4-(N-allyloxycarbonylaminomethyl)phenyl]-1-allyloxycarbonylpyrrolidine 
• 228267-29-6 (3R)-N-allyloxycarbonyl-1-(4-tert-butyldimethylsiloxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutylamine 
• 262846-09-3 (2S,4S)-2-[4-(Allyloxycarbonylamino-methyl)-phenyl]-4-mercapto-pyrrolidine-1-carboxylic acid allyl ester 
• 304655-64-9 [(R)-1-(4-Azidomethyl-phenyl)-3,4-dihydroxy-butyl]-carbamic acid allyl ester 
• 263155-23-3 Toluene-4-sulfonic acid (2R,4R)-4-allyloxycarbonylamino-4-[4-(allyloxycarbonylamino-methyl)-phenyl]-2-(tert-butyl-dimethyl-silanyloxy)-butyl ester 
• 263155-22-2 Toluene-4-sulfonic acid (2R,4R)-4-allyloxycarbonylamino-4-[4-(allyloxycarbonylamino-methyl)-phenyl]-2-hydroxy-butyl ester 

Relevant academic research and scientific papers

Synthesis of J-111,347, a novel 1β-methylcarbapenem with broad-spectrum antibacterial activity

Synthesis of J-111,347 (1), a new 1β-methylcarbapenem with broad- spectrum antibacterial activity including that against methicillin-resistant Staphylococcus aureus (MRSA) and Pseudomonas aeruginosa, was achieved via diastereoselective preparation of a side-chain thiol 3 from an optically active (R)3,4-dihydroxybutanal 4.

Discovery of novel trans-3,5-disubstituted pyrrolidinylthio-1β-methylcarbapenems

Novel trans-3,5-disubstituted pyrrolidinylthio-1β-methylcarbapenems were designed and synthesized to provide J-111,347 (1a) as the first example of an exceptionally broad-spectrum antibiotic, showing activity against methicillin-resistant Staphyloccocus aureus (MRSA) as well as Pseudomonas aeruginosa. Further derivation of 1a afforded J-111,225 (2a), J-114,870 (3a), and J-114,871 (3b), which showed improved safety profiles and retained broad-spectrum antibacterial activities. Copyright (C) 2000 Elsevier Science Ltd.

Structure-activity relationships of trans-3,5-disubstituted pyrrolidinylthio- 1β-methylcarbapenems. Part 1:J-111,347 and related compounds

1β-Methylcarbapenems having various 3,5-disubstituted pyrrolidinylthio- side chains at C-2 were designed and synthesized. Evaluation of their antibacterial activities indicated that J-111,347 (1a) is the first example of an extremely broad spectrum antibiotic showing activity against methicillin-resistant Staphylococcus aureus (MRSA) as well as Pseudomonas aeruginosa.