158527-21-0

Basic information

• Product Name: tert-butyl (2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine-1-carboxylate
• Synonyms: tert-butyl (2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine-1-carboxylate
• CAS NO: 158527-21-0
• Molecular Weight: 403.605
• Mol File: 158527-21-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: tert-butyl (2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine-1-carboxylate(158527-21-0)
• EPA Substance Registry System: tert-butyl (2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine-1-carboxylate(158527-21-0)

Safety Data

• Hazardous Substances Data: 158527-21-0(Hazardous Substances Data)

Upstream product

• 158527-18-5 ((S)-1-Benzyl-2-oxo-tridec-3-ynyl)-carbamic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 69765-57-7 undecynyllithium 
• 87694-53-9 Boc-Phe-OH N,O-dimethyl hydroxamate 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 173728-51-3 (2S,3R,4S)-2-Benzyl-3,4-bis-benzyloxy-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 175550-97-7 (3S,4R,5S)-5-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-one 
• 175550-94-4 (3S,4R,5S)-5-Benzyl-3,4-bis-benzyloxy-1-(4-methoxy-benzyl)-pyrrolidin-2-one 
• 175550-95-5 (2S,3S)-tert-butyl 2-benzyl-3-((tert-butyldimethylsilyl)oxy)-5-oxopyrrolidine-1-carboxylate 
• 175550-98-8 (2S,3R,4S)-2-Benzyl-3,4-dihydroxy-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 109579-10-4 (4S,5R)-N-(((tert)-butyloxy)carbonyl)-5-benzyl-4-hydroxy-2-pyrrolidinone 
• 205491-21-0 (2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-nonyl-2-vinyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 205491-17-4 Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-butyl ester 
• 205491-09-4 {(R)-1-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-decyl}-carbamic acid tert-butyl ester 

Downstream Products

• 210964-94-6 (+)-(2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine 
• 125356-66-3 (+)-preussin 

Relevant articles and documents

Versatile one-pot reductive alkylation of lactams/amides via amide activation: Application to the concise syntheses of bioactive alkaloids (±)-bgugaine, (±)-coniine, (+)-preussin, and (-)-cassine

Direct entry: One-pot reductive alkylation of lactams/amides with Grignard reagents has been realized via lactam/amide activation with Tf2O. This method opens a direct entry to α-alkylated amines. The versatility of the method is illustrated by the concise syntheses of bioactive alkaloids (±)-bgugaine, (±)-coniine, (+)-preussin, and (?)-cassine.

Novel route to the synthesis of hydroxylated pyrrolidine derivatives via the intramolecular reaction of γ-aminoallylstannane with aldehyde. Total synthesis of (+)-preussin

The thermal cyclization of γ-aminoallylstannane (8) having an aldehyde group gave β-hydroxypyrrolidine derivative (9a) as a sole product. This methodology was applied successfully to the total synthesis of (+)-preussin.

A Concise Synthesis of the Antifungal Agent (+)-Preussin

The antifungal agent (+)-preussin (1) was synthesized in five efficient transformations from t-Boc-(S)-phenylalanine.The key step involved the Hg(II)-mediated ring closure of ynone 4, a 5-endo-dig process.