651359-09-0

Basic information

• Product Name: Pyrrolidine, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-methyl-5-nonyl-2-(phenylmethyl )-, (2S,3S,5R)-
• CAS NO: 651359-09-0
• Molecular Formula: C27H49NOSi
• Molecular Weight: 431.778
• Mol File: 651359-09-0.mol

Chemical Properties

• CAS DataBase Reference: Pyrrolidine, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-methyl-5-nonyl-2-(phenylmethyl )-, (2S,3S,5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrrolidine, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-methyl-5-nonyl-2-(phenylmethyl )-, (2S,3S,5R)-(651359-09-0)
• EPA Substance Registry System: Pyrrolidine, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-methyl-5-nonyl-2-(phenylmethyl )-, (2S,3S,5R)-(651359-09-0)

Safety Data

• Hazardous Substances Data: 651359-09-0(Hazardous Substances Data)

Upstream product

• 892859-51-7 (-)-(R_S,4R)-4-(2-methyl-propane-2-sulfinylamino)tridecene 
• 109579-09-1 (5S)-5-benzyl-4-hydroxy-1-t-butoxycarbonylpyrrol-2(5H)-one 
• 50-00-0 formaldehyd 
• 39691-62-8 nonylmagnesium bromide 
• 175550-95-5 (2S,3S)-tert-butyl 2-benzyl-3-((tert-butyldimethylsilyl)oxy)-5-oxopyrrolidine-1-carboxylate 
• 109579-10-4 (4S,5S)-5-Benzyl-1-(tert-butyloxycarbonyl)-4-hydroxypyrrolidin-2-one 
• 100-39-0 benzyl bromide 
• 229981-33-3 tert-butyl (2S,3R)-2-benzyl-3--5-oxo-1-pyrrolidinecarboxylate 
• 651358-97-3 4-[1-tert-butyldimethylsilyloxy-2-(4-methylphenylsulfinyl)-(1R,2Ss)-ethyl]-3-methyl-5-phenyl-(4S,5R)-1,3-oxazolan-2-one 
• 651358-95-1 2-bromo-3-tert-butyldimethylsilyloxy-(4Ss)-(4-methylphenylsulfinyl)-1-phenyl-(1R,2R,3S)-butan-1-ol 
• 651358-94-0 (Rs)-2-tert-butyldimethylsilyloxy-4-phenyl-(2R,3E)-3-butenyl 4-methylphenyl sulfoxide 
• 651359-04-5 2-tert-butyldimethylsilyloxy-2-[3-methyl-2-oxo-5-phenyl-(4S,5R)-1,4-oxazolan-4-yl]-acetaldehyde 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 95482-80-7 1-(4-methylphenylsulfinyl)-4-phenyl-(2R,3E)-3-buten-2-ol 

Downstream Products

• 125356-66-3 (+)-preussin 

Relevant articles and documents

An efficient approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones through a stereoselective tandem Barbier process: divergent syntheses of (3R,4S)-statines, (+)-preussin and (?)-hapalosin

A diastereoselective approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones 1 (P1 = TBS, P2 = H) has been developed through a stereoselective tandem Barbier process of (R,SRS)-8 with alkyl and aryl bromide. The stereochemistry at the C-5 stereogenic center of the trans-4-hydroxy-5-substituted 2-pyrrolidinones was solely controlled by α-alkoxy substitution. This effective approach was successfully used to prepare a variety of substituted (3R,4S)-statines 2. In addition, two bioactive natural products of (+)-preussin 4 and hapalosin 5 were effectively synthesized through this stereoselective tandem Barbier process.

Asymmetric synthesis of 2,5-disubstituted 3-hydroxypyrrolidines based on stereodivergent intramolecular iridium-catalyzed allylic aminations

Intramolecular iridium-catalyzed allylic aminations of homochiral (E)-6-N-nosylaminohept-2-en-1-yl methyl carbonates were investigated. The relative position of the 2,5-substituents of the resulting pyrrolidines was found to be controlled by using both enantiomers (4 and 5) of the appropriate chiral ligand, demonstrating a simple and highly stereodivergent synthetic protocol. Selected trans- and cis-2,5-disubstituted 3-hydroxypyrrolidines (2a and 18a) were converted to (+)-bulgecinine (6) and (+)-preussin (7), respectively.

A concise stereoselective synthesis of Preussin, 3-epi-Preussin, and analogues

A new stereoselective synthesis of the antifungal and antitumor agents Preussin and 3-epi-Preussin via a Pd-catalyzed carboamination of a protected amino alcohol is described. The key transformation leads to simultaneous formation of the N-C2 bond and the C1′-aryl bond, and allows installation of the aryl group one step from the end of the sequence. This strategy permits the facile construction of a variety of preussin analogues bearing different aromatic groups.

A novel and stereospecific synthesis of (+)-preussin

A novel and stereospecific approach to (+)-preussin that would permit the synthesis of analogs for structure activity relationship studies, is disclosed. The key step includes the regio- and stereoselective elaboration of a bromohydrin via intramolecular sulfinyl group participation.