223117-76-8

Upstream product

• 223118-72-7 (R)-5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(dimethyl-phenyl-silanyl)-5-oxo-pentanoic acid tert-butyl ester 
• 100-51-6 benzyl alcohol 
• 1130247-32-3 (3'R,4S)-3-{4-tert-butoxycarbonyl-3-[dimethyl(phenyl)silyl]-1-oxobutyl}-5,5-di(2-methoxy-5-methylphenyl)-4-isopropyloxazolidin-2-one 

Downstream Products

• 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 
• 223117-82-6 (R)-3-(Dimethyl-phenyl-silanyl)-pentanedioic acid tert-butyl ester methyl ester 
• 223117-54-2 (S)-3-(Dimethyl-phenyl-silanyl)-pentanedioic acid monomethyl ester 
• 196491-87-9 [(1S,2S)-1-Benzyl-2-(dimethyl-phenyl-silanyl)-4-oxo-tridecyl]-carbamic acid benzyl ester 
• 196491-85-7 (2R,3S)-2-Benzyl-3-(dimethyl-phenyl-silanyl)-4-(2-nonyl-[1,3]dioxolan-2-yl)-butyric acid methyl ester 
• 196491-88-0 (2S,3S,5R)-2-Benzyl-3-(dimethyl-phenyl-silanyl)-5-nonyl-pyrrolidine-1-carboxylic acid ethyl ester 
• 196491-84-6 (S)-3-(Dimethyl-phenyl-silanyl)-4-(2-nonyl-[1,3]dioxolan-2-yl)-butyric acid methyl ester 

Relevant academic research and scientific papers

An efficient asymmetric desymmetrization of prochiral glutaric anhydrides with SuperQuat chiral oxazolidin-2-ones

The asymmetric desymmetrization of 3-substituted glutaric anhydrides 1 bearing silyl, aryl and alkyl groups with the lithium salt of chiral oxazolidin-2-ones has been studied. The effects of the substituents at the 4- and 5-positions of the oxazolidin-2-ones on the diastereoselectivity of the anhydride opening were studied in detail. A SuperQuat chiral oxazolidin-2-one 2e with 5,5-diaryl substituents showed optimum selectivity.

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.