159154-02-6

Basic information

• Product Name: (2S,3S,5R)-3-Acetoxy-1-ethoxycarbonyl-2-benzyl-5-nonylpyrrolidine
• Synonyms: (2S,3S,5R)-3-Acetoxy-1-ethoxycarbonyl-2-benzyl-5-nonylpyrrolidine
• CAS NO: 159154-02-6
• Molecular Weight: 417.589
• Mol File: 159154-02-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2S,3S,5R)-3-Acetoxy-1-ethoxycarbonyl-2-benzyl-5-nonylpyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,5R)-3-Acetoxy-1-ethoxycarbonyl-2-benzyl-5-nonylpyrrolidine(159154-02-6)
• EPA Substance Registry System: (2S,3S,5R)-3-Acetoxy-1-ethoxycarbonyl-2-benzyl-5-nonylpyrrolidine(159154-02-6)

Safety Data

• Hazardous Substances Data: 159154-02-6(Hazardous Substances Data)

Upstream product

• 39691-62-8 nonylmagnesium bromide 
• 108-24-7 acetic anhydride 
• 159154-01-5 (2S,3S,5R)-3-acetyl-2-benzyl-1-(ethoxycarbonyl)-5-nonylpyrrolidine 
• 223118-42-1 [(1S,2S)-1-Benzyl-2-(dimethyl-phenyl-silanyl)-3-(2-nonyl-[1,3]dioxolan-2-yl)-propyl]-carbamic acid benzyl ester 
• 223118-85-2 (2R,3S)-2-Benzyl-3-(dimethyl-phenyl-silanyl)-4-(2-nonyl-[1,3]dioxolan-2-yl)-butyric acid 
• 196491-86-8 (2R,3S)-2-Benzyl-3-(dimethyl-phenyl-silanyl)-4-(2-nonyl-[1,3]dioxolan-2-yl)-butyramide 
• 223117-48-4 methyl (3S)-3-[dimethyl(phenyl)silyl]-5-oxotetradecanoate 
• 196491-87-9 [(1S,2S)-1-Benzyl-2-(dimethyl-phenyl-silanyl)-4-oxo-tridecyl]-carbamic acid benzyl ester 
• 223118-05-6 (S)-4-Benzyl-3-[(S)-3-(dimethyl-phenyl-silanyl)-4-(2-nonyl-[1,3]dioxolan-2-yl)-butyryl]-oxazolidin-2-one 
• 196491-83-5 (S)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(dimethyl-phenyl-silanyl)-tetradecane-1,5-dione 
• 196491-85-7 (2R,3S)-2-Benzyl-3-(dimethyl-phenyl-silanyl)-4-(2-nonyl-[1,3]dioxolan-2-yl)-butyric acid methyl ester 
• 196491-84-6 (S)-3-(Dimethyl-phenyl-silanyl)-4-(2-nonyl-[1,3]dioxolan-2-yl)-butyric acid methyl ester 

Downstream Products

• 125356-66-3 (+)-preussin 

Relevant articles and documents

Desymmetrization of 3-dimethyl(phenyl)silyl glutaric anhydride with Evans' oxazolidinone: An application to stereocontrolled synthesis of the antifungal agent (+)-preussin

A stereoselective total synthesis of (+)-preussin (1) has been achieved from the a-symmetric 3-dimethyI(phenyl)silyl substituted glutaric anhydride 4 featuring its desymmetrization using Evans' oxazolidinone 10. The first homochiral intermediate, the glutarate half-ester 9 was obtained from both the diastereoisomeric acids lia, and 12a in a convergent fashion. The dimethyl(phenyl)silyl group is not only acting as a masked hydroxy group but also restricts elimination reactions, and facilitates Curtius reaction. It also stereodirects ester enolate alkylation of 18, and hydrogenation of intermediate Δ1-pyrroline 5.

Enantioselective total synthesis of either enantiomer of the antifungal antibiotic preussin (L-657,398) from (S)-phenylalanine

Enantioselective total syntheses of the antifungal agent (+)-preussin (1) and its enantiomer (-)-1 from (S)-phenylalanine are described. The central transformations are protic acid-promoted aza-Cope rearrangement - Mannich cyclization reactions (12 → 19 and 13 → 27). Retro-Mannich fragmentation-Mannich cyclization (27 → 28) is key to the formation of (-)-1. This study demonstrates, for the first time, that enantioenriched substituted pyrrolidines can be prepared using the aza-Cope-Mannich rearrangement.