223437-40-9

Upstream product

• 186581-53-3 diazomethane 
• 134208-73-4 (S)-3-Hydroxy-4-((S)-1-phenyl-ethylcarbamoyl)-butyric acid 
• 116159-66-1 dimethyl 3-dimethyl(phenyl)silylpentan-1,5-dioate 
• 196491-73-3 dimethyl 2-methoxycarbonyl-3-dimethyl(phenyl)silyl-1,5-pentanedioate 
• 223436-83-7 3-(Dimethyl-phenyl-silanyl)-pentanedioic acid 
• 196491-79-9 (R)-5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(dimethyl-phenyl-silanyl)-5-oxo-pentanoic acid benzyl ester 
• 196491-90-4 (R)-5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(dimethyl-phenyl-silanyl)-5-oxo-pentanoic acid 
• 223437-38-5 (S)-5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-hydroxy-5-oxo-pentanoic acid ((S)-1-phenyl-ethyl)-amide 
• 196491-68-6 3-[dimethyl(phenyl)silyl]glutaric anhydride 
• 41527-39-3 dimethyl (2E)-pent-2-enedioate 

Downstream Products

• 121331-23-5 (3S,1'S)-3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-5-[(1-phenylethyl)amino]-5-oxopentanoic acid, methyl ester 

Relevant academic research and scientific papers

Desymmetrization of prochiral anhydrides with Evans' oxazolidinones: An efficient route to homochiral glutaric and adipic acid derivatives

The prochiral recognition between enantiotopic carbonyl groups in the reaction of 3-substituted glutaric and 3,4-disubstituted adipic anhydrides with anions of Evans' oxazolidinones has been investigated. Each of the σ-symmetric anhydrides provided a diastereoisomeric mixture of half-acids which were separated either by fractional crystallization or by column chromatography of their esters. The diastereoselectivity of the desymmetrization reaction is dependent on the substituents present in the anhydrides.

A silicon controlled total synthesis of the antifungal agent (+)-preussin

A stereoselective total synthesis of (+)-preussin has been achieved from a meso anhydride featuring a dimethyl(phenyl)silyl group as a masked hydroxy group which also restricts elimination reactions, stereodirects hydrogenation and ester enolate alkylation, and facilitates Curtius reaction.