75659-16-4

Basic information

• Product Name: (3S-trans)-3-[(t-Butyloxycarbonyl)aMino]-4-Methyl-2-oxo-1-(phenylMethoxy)azetidine
• Synonyms: (3S-trans)-3-[(t-Butyloxycarbonyl)aMino]-4-Methyl-2-oxo-1-(phenylMethoxy)azetidine
• CAS NO: 75659-16-4
• Molecular Formula: C₁₆H₂₂N₂O₄
• Molecular Weight: 306.35688
• Mol File: 75659-16-4.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3S-trans)-3-[(t-Butyloxycarbonyl)aMino]-4-Methyl-2-oxo-1-(phenylMethoxy)azetidine(CAS DataBase Reference)
• NIST Chemistry Reference: (3S-trans)-3-[(t-Butyloxycarbonyl)aMino]-4-Methyl-2-oxo-1-(phenylMethoxy)azetidine(75659-16-4)
• EPA Substance Registry System: (3S-trans)-3-[(t-Butyloxycarbonyl)aMino]-4-Methyl-2-oxo-1-(phenylMethoxy)azetidine(75659-16-4)

Safety Data

• Hazardous Substances Data: 75659-16-4(Hazardous Substances Data)

Upstream product

• 75624-30-5 O-benzyl-α-N-t-BOC-D-threonine 
• 622-33-3 N-benzyloxyamine 
• 75624-31-6 tert-butyl ((2S,3R)-1-((benzyloxy)amino)-3-hydroxy-1-oxobutan-2-yl)carbamate 
• 2592-18-9 Boc-Thr-OH 
• 75624-30-5 O-benzyl-α-N-t-BOC-D,L-allo-threonine hydroxamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 2592-18-9 N-t-BOC-D,L-allo-threonine 
• 1972-28-7 diethylazodicarboxylate 

Downstream Products

• 80542-48-9 (3S-trans)-3-(t-butyloxycarbonylamino)-1-hydroxy-4-methyl-2-azetidinone 
• 286939-11-5 (2S,3S)-3-((benzyloxy)amino)-2-((tert-butoxycarbonyl)amino)butanoic acid 
• 286939-12-6 (2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-[(N-benzyloxy-N-methyl)amino]butanoic acid 
• 87791-60-4 4-methyl-3-<(tert-butoxycarbonyl)amino>-1-dibenzylphosphoryl-2-azetidinone 
• 82933-50-4 (2S,3S)-1-(benzyloxy)-2-methyl-4-oxoazetidin-3-ylammonium tosylate salt 

Relevant articles and documents

Synthetic Sansanmycin Analogues as Potent Mycobacterium tuberculosis Translocase i Inhibitors

Herein, we report the design and synthesis of inhibitors of Mycobacterium tuberculosis (Mtb) phospho-MurNAc-pentapeptide translocase I (MurX), the first membrane-associated step of peptidoglycan synthesis, leveraging the privileged structure of the sansanmycin family of uridylpeptide natural products. A number of analogues bearing hydrophobic amide modifications to the pseudo-peptidic end of the natural product scaffold were generated that exhibited nanomolar inhibitory activity against Mtb MurX and potent activity against Mtb in vitro. We show that a lead analogue bearing an appended neopentylamide moiety possesses rapid antimycobacterial effects with a profile similar to the frontline tuberculosis drug isoniazid. This molecule was also capable of inhibiting Mtb growth in macrophages where mycobacteria reside in vivo and reduced mycobacterial burden in an in vivo zebrafish model of tuberculosis.

2-oxoazetidin-1-yloxy acetic acids and analogs

Antibiotic activity is exhibited by β-lactams having an STR1 substituent (and analogs thereof) in the 1-position and an acylamino substituent in the 3-position.

2-OXO-1-AZETIDINESULFONIC ACID SALTS

Antibacterial activity is exhibited by beta-lactams having a sulfonic acid salt substituent in the 1-position and an amino or acylamino substituent in the 3-position.