211866-70-5

Basic information

• Product Name: (1R,4R,5S)-1-[1(S)-Hydroxy-2-methylpropyl]-4-propyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
• Synonyms: MLN-519; LDP-519; PS-519
• CAS NO: 211866-70-5
• Molecular Formula: C₁₂H₁₉NO₄
• Molecular Weight: 241.28953
• Mol File: 211866-70-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,4R,5S)-1-[1(S)-Hydroxy-2-methylpropyl]-4-propyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4R,5S)-1-[1(S)-Hydroxy-2-methylpropyl]-4-propyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione(211866-70-5)
• EPA Substance Registry System: (1R,4R,5S)-1-[1(S)-Hydroxy-2-methylpropyl]-4-propyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione(211866-70-5)

Safety Data

• Hazardous Substances Data: 211866-70-5(Hazardous Substances Data)

Upstream product

• 220805-49-2 3-(5S-isopropyl-4S-methoxycarbonyl-2-phenyl-4,5-dihydrooxazol-4-yl)-3S-hydroxy-2R-n-propyl-N,N-diethylpropionamide 
• 220805-27-6 3-(3-benzyloxymethyl-2R-n-propylpropionyl)-4S-benzyloxazolidin-2-one 
• 220805-54-9 3S-hydroxy-2R-(1S-hydroxy-2-methylpropyl)-4R-n-propyl-5-oxopyrrolidine-2-carboxylic acid methyl ester 
• 220805-35-6 2R-benzyloxymethylpentanoic acid diethylamide 
• 220805-67-4 (2R,3S)-2-azo-4-methyl-3-benzoyloxypentanoic acid methyl ester 
• 220805-66-3 (2S,3S)-2-bromo-4-methyl-3-benzoyloxypentanoic acid methyl ester 
• 220805-31-2 2R-benzyloxymethylpentanoic acid 
• 220805-40-3 2R-hydroxymethylpentanoic acid diethylamide 
• 220805-44-7 2R-formylpentanoic acid diethylamide 
• 220805-65-2 (2R,3S)-2,3-dihydroxy-4-methylpentanoic acid methyl ester 
• 143868-89-7 3-(1-oxopentyl)-4(S)-(phenylmethyl)-2-oxazolidinone 
• 148906-20-1 (4R,5S)-5-isopropyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester 
• 638-29-9 n-valeryl chloride 
• 20515-15-5 methyl (2E)-4-methylpent-2-enoate 

Relevant articles and documents

A novel and efficient synthesis of a highly active analogue of clasto-lactacystin β-lactone

Herein, we describe a new convergent synthesis of a more potent analogue of clasto-lactacystin β-lactone (2), PS-519 compound 4, which is currently in preclinical development for the treatment of ischemia-reperfusion injury in stroke and myocardial infarction. The synthetic strategy relies on building two intermediates (an oxazoline and an aldehyde) which are joined through a doubly diastereoselective aldol reaction, setting up the requisite unichiral centers in the final product (4). The facial selectivity and ultimate stereocontrol are achieved by employing a trivalent aluminum Lewis acid, Me2AlCl, in a chelation-induced reaction which yields a single aldol adduct. The efficiency of the synthetic approach has allowed for the preparation of multigram quantities of clinical grade material, which will support Phase I studies.