196491-87-9

Basic information

• Product Name: [(1S,2S)-1-Benzyl-2-(dimethyl-phenyl-silanyl)-4-oxo-tridecyl]-carbamic acid benzyl ester
• Synonyms: [(1S,2S)-1-Benzyl-2-(dimethyl-phenyl-silanyl)-4-oxo-tridecyl]-carbamic acid benzyl ester
• CAS NO: 196491-87-9
• Molecular Weight: 571.875
• Mol File: 196491-87-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: [(1S,2S)-1-Benzyl-2-(dimethyl-phenyl-silanyl)-4-oxo-tridecyl]-carbamic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [(1S,2S)-1-Benzyl-2-(dimethyl-phenyl-silanyl)-4-oxo-tridecyl]-carbamic acid benzyl ester(196491-87-9)
• EPA Substance Registry System: [(1S,2S)-1-Benzyl-2-(dimethyl-phenyl-silanyl)-4-oxo-tridecyl]-carbamic acid benzyl ester(196491-87-9)

Safety Data

• Hazardous Substances Data: 196491-87-9(Hazardous Substances Data)

Upstream product

• 196491-79-9 (R)-5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(dimethyl-phenyl-silanyl)-5-oxo-pentanoic acid benzyl ester 
• 223117-91-7 (R)-3-(Dimethyl-phenyl-silanyl)-pentanedioic acid benzyl ester methyl ester 
• 223117-48-4 methyl (3S)-3-[dimethyl(phenyl)silyl]-5-oxotetradecanoate 
• 223117-54-2 (S)-3-(Dimethyl-phenyl-silanyl)-pentanedioic acid monomethyl ester 
• 196491-90-4 (R)-5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(dimethyl-phenyl-silanyl)-5-oxo-pentanoic acid 
• 196491-84-6 (S)-3-(Dimethyl-phenyl-silanyl)-4-(2-nonyl-[1,3]dioxolan-2-yl)-butyric acid methyl ester 
• 39691-62-8 nonylmagnesium bromide 
• 223118-42-1 [(1S,2S)-1-Benzyl-2-(dimethyl-phenyl-silanyl)-3-(2-nonyl-[1,3]dioxolan-2-yl)-propyl]-carbamic acid benzyl ester 
• 196491-68-6 3-[dimethyl(phenyl)silyl]glutaric anhydride 
• 223118-72-7 (R)-5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(dimethyl-phenyl-silanyl)-5-oxo-pentanoic acid tert-butyl ester 
• 223117-71-3 (S)-5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(dimethyl-phenyl-silanyl)-5-oxo-pentanoic acid tert-butyl ester 
• 223118-78-3 (S)-3-(Dimethyl-phenyl-silanyl)-pentanedioic acid benzyl ester tert-butyl ester 
• 223117-76-8 (3R)-benzyl tert-butyl 3-[dimethyl(phenyl)silyl]pentane-1,5-dioate 
• 223118-85-2 (2R,3S)-2-Benzyl-3-(dimethyl-phenyl-silanyl)-4-(2-nonyl-[1,3]dioxolan-2-yl)-butyric acid 

Downstream Products

• 125356-66-3 (+)-preussin 
• 159154-02-6 (2S,3S,5R)-3-Acetoxy-1-ethoxycarbonyl-2-benzyl-5-nonylpyrrolidine 
• 196491-88-0 (2S,3S,5R)-2-Benzyl-3-(dimethyl-phenyl-silanyl)-5-nonyl-pyrrolidine-1-carboxylic acid ethyl ester 

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.