210964-94-6

Basic information

• Product Name: (+)-(2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine
• Synonyms: (+)-(2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine
• CAS NO: 210964-94-6
• Molecular Weight: 303.488
• Mol File: 210964-94-6.mol

Chemical Properties

• CAS DataBase Reference: (+)-(2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine(210964-94-6)
• EPA Substance Registry System: (+)-(2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine(210964-94-6)

Safety Data

• Hazardous Substances Data: 210964-94-6(Hazardous Substances Data)

Upstream product

• 210964-93-5 (2S,3S)-2-Benzyl-5-oxo-3-[(R)-1-(2,4,6-triisopropyl-phenyl)-ethoxy]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 210964-89-9 (+)-(4S,5S)-5-benzyl-4-[(1R)-1-(2,4,6-triisopropylphenyl)ethoxy]-2-pyrrolidinone 
• 219969-15-0 (4S,5S)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-benzyl-5-(2-hydroxyundecyl)-1,3-oxazolidine 
• 219969-14-9 (4S,5S)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-benzyl-5-formylmethyl-1,3-oxazolidine 
• 219969-13-8 (4S,5S)-tert-butyl 2,2-dimethyl-4-benzyl-5-prop-2-enyl-1,3-oxazolidine 
• 129778-81-0 (1S,2S)-(tert-butoxy)-N-[2-hydroxy-1-benzylpent-4-enyl]carboxamide 
• 317322-36-4 2-((4S,5S)-4-benzyl-2-phenyl-4,5-dihydro-oxazol-5-yl)-N-methoxy-N-methyl-acetamide 
• 208935-28-8 (4S-trans)-4,5-dihydro-4-benzyl-2-phenyl-5-vinyloxazoline 
• 257296-71-2 (4S-trans)-4,5-dihydro-4-benzyl-5-(2-hydroxyethyl)-2-phenyloxazoline 
• 298208-76-1 (4S-trans)-4,5-dihydro-4-benzyl-2-phenyloxazoline-5-acetic Acid 
• 35593-57-8 (S)-N-(1-oxo-3-phenylpropan-2-yl)benzamide 
• 5267-65-2 (S)-N-(1-hydroxy-3-phenylpropan-2-yl)benzamide 
• 317322-37-5 1-((4S,5S)-4-benzyl-2-phenyl-4,5-dihydro-oxazol-5-yl)-undecan-2-one 
• 158527-21-0 tert-butyl (2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine-1-carboxylate 

Downstream Products

• 125356-66-3 (+)-preussin 

Relevant articles and documents

Alkoxyallene-based syntheses of preussin and its analogs and their cytotoxicity

Short syntheses of oxa-preussin, racemic preussin and (-)-preussin are reported. Starting from a racemic 3-nonyl-substituted methoxyallene derivative, its lithiation and addition to phenylethanal provided the corresponding allenyl alcohol that was converted into two diastereomeric dihydrofuran derivatives by silver nitrate-catalyzed 5-endo-trig cyclization. The acid hydrolysis of the enol ether moiety gave heterocyclic ketones and subsequent highly stereoselective reductions with l-selectride furnished 2-benzyl-5-nonylfuran-3-ol derivatives in good overall yield. The major all-cis-diastereomer has the skeleton and relative configuration of preussin and is hence called oxa-preussin. An analogous sequence with the same allene, but an N-sulfonyl imine as the electrophile, finally led to racemic preussin. The stereoselectivities of the individual steps are discussed in detail. With an enantiopure 2-benzyl-5-nonylpyrrolidin-3-one intermediate the preparation of (-)-preussin with an enantiomeric ratio of >95:5 could be accomplished in a few steps. The sign of the optical rotation of this product finally proved the absolute configurations of its precursors and demonstrated that our chiral auxiliary-based route led to the antipode of the natural product. The cytotoxicity of several of the prepared heterocycles against MCF-7 tumor cells was investigated and five compounds, including racemic and enantiopure (-)-preussin, were identified as highly cytotoxic with IC50 values in the range of 3-6 μM.

Facile and efficient total synthesis of (+)-preussin.

[structure] The enantioselective total synthesis of (+)-preussin, a potent antifungal agent, has been achieved. The key steps are a Pd(0)-catalyzed oxazoline-forming reaction from L-phenylalanine, hydrogenolysis, and subsequent diastereoselective reductive cyclization of the intermediate aminoketone to pyrrolidine using Pearlman's catalyst.

Practical asymmetric approach to pyrrolidinones: Efficient synthesis of (+)-preussin and (-)-AHPPA

A novel, dichloroketene-chiral enol ether cycloaddition-based synthesis of enantiopure (+)-preussin and (-)-AHPPA has been realized. The efficient, highly stereoselective approach, which involves a Beckmann ring expansion reaction to access the key pyrrolidinone, proceeds in ca. 16% overall yield for each of the compounds.

Stereoselective synthesis of the antifungal antibiotic (+)-preussin

A concise total synthesis of enantiopure (+)-preussin (1) from L- phenylalanine (3) is described. The key steps involve i) syn-selective formation of the 1,2-amino alcohol fragment 2, via chelation controlled addition of allylmagnesium bromide to N-Boc-phenylalaninal, and ii) L- selectride mediated stereoselective reduction of the ketone 8 to the alcohol derivative 9 with the required stereochemistry for final cyclization.