110652-75-0

Upstream product

• 625-38-7 but-3-enoic acid 
• 86170-45-8 benzyl 3-butenoate 
• 100-51-6 benzyl alcohol 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 133039-03-9 (3R)-3,4-dihydroxybutyric acid benzyl ester 
• 110672-01-0 (E)-3-Hydroxy-7-trimethylsilanyl-hept-5-enoic acid benzyl ester 
• 110652-83-0 (Z)-3-Hydroxy-7-trimethylsilanyl-hept-5-enoic acid benzyl ester 
• 110652-90-9 (3R,5R)-3,5-Dihydroxy-hept-6-enoic acid benzyl ester 
• 110652-90-9 (3R,5S)-3,5-Dihydroxy-hept-6-enoic acid benzyl ester 
• 669065-48-9 (R)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-butyric acid benzyl ester 
• 669065-40-1 (R)-4-(tert-butyldimethylsilyloxy)-3-methoxy-butyric acid benzyl ester 
• 586952-09-2 benzyl (E)-4-hydroxy-2-butenoate 
• 110930-71-7 phenylmethyl 4-chloro-3-hydroxybutanoate 
• 110652-79-4 3-Hydroxy-7-trimethylsilanyl-hept-5-ynoic acid benzyl ester 
• 586952-15-0 benzyl (E)-4-p-toluenesulfonylaminocarbonyloxy-2-butenoate 
• 586952-21-8 benzyl (3-p-toluenesulfonyl-1,3-oxazolidin-2-on-4-yl)acetate 

Relevant academic research and scientific papers

Homochiral oxazolidin-2-ones and imidazolidin-2-ones by tandem nucleophilic addition-conjugate addition

Treatment of both primary alcohols 1a,b and secondary amines 1c,d, tethered to a Michael acceptor with (R)-phenylethyl isocyanate in the presence of DBU gave in good yield and high stereoselection diastereomeric mixtures of oxazolidin-2-ones 2a,b and 3a,b

SO2F2-Mediated Epoxidation of Olefins with Hydrogen Peroxide

An inexpensive, mild, and highly efficient epoxidation protocol has been developed involving bubbling SO2F2 gas into a solution of olefin, 30% aqueous hydrogen peroxide, and 4 N aqueous potassium carbonate in 1,4-dioxane at room temperature for 1 h with the formation of the corresponding epoxides in good to excellent yields. The novel SO2F2/H2O2/K2CO3 epoxidizing system is suitable to a variety of olefinic substrates including electron-rich and electron-deficient ones.

Synthesis of 2-Fluoroacetoacetic Acid and 4-Fluoro-3-hydroxybutyric Acid

The butyric acid scaffold is the base structure of several human metabolites that serve diverse and prominent biochemical roles including as oxidative sources of cellular energy and as substrates for biosynthesis. Derivatization of metabolites through incorporation of fluorine often alters bioactivity and can facilitate detection and analysis by nuclear magnetic resonance or positron emission tomography depending upon the fluorine isotope employed. We describe the synthesis of two new fluorinated butyric acids (and three related esters) that are derivatives of the metabolites acetoacetic acid and 3-hydroxybutyric acid. 4-Fluoro-3-hydroxybutyric acid is prepared from epoxy ester precursors via ring opening by triethylamine trihydrofluoride. 2-Fluoroacetoacetic acid is prepared by electrophilic fluorination of an acid-labile β-keto ester. The gradual pH-dependent decarboxylation of 2-fluoroacetoacetic acid is investigated by 19 F NMR spectroscopy.

Organocatalytic asymmetric oxy-Michael addition to a γ-hydroxy- α,β-unsaturated thioester via hemiacetal intermediates

We report an asymmetric oxy-Michael addition to a γ-hydroxy-α, β-unsaturated thioester via hemiacetal intermediates in the presence of Cinchona-alkaloid-thiourea-based bifunctional organocatalysts. This method provides a novel enantioselective route to β-hydroxy carboxyl compounds, which in turn can be used to synthesize valuable chiral building blocks.

Stereoselective preparation of 3-alkanoylprop-2-en-1-ol derivatives

3-Alkanoylprop-2-en-1-ol derivatives were prepared stereoselectively by ring-opening reaction of β,γ-epoxyketone with amines. Georg Thieme Verlag Stuttgart.

Stereoselective synthesis of trans-4,5-disubstituted oxazolidin-2-ones by intramolecular conjugate addition of N-p-toluenesulfonyl carbamates

p-Toluenesulfonyl carbamates (2a-d) were prepared starting from allylic alcohols (3), in which the double bond is conjugated with an electron withdrawing group. In the presence of a catalytic amount of DBU, an intramolecular cyclisation occurred, leading

Lipase-catalyzed resolution of esters of 4-chloro-3-hydroxybutanoic acid: Effects of the alkoxy group and solvent on the enantiomeric ratio

Various lipases have been investigated for their potential use as catalysts for the resolution of esters of 4-chloro-3-hydroxybutanoic acid via transesterification in organic solvents. Rhizomucor miehei lipase was found to be the most efficient lipase, with the enantiomeric ratio (E) being dependent upon of the nature of the alkoxy group of the ester and the resolution medium. Higher E-values were obtained when transesterification was performed in benzene or carbon tetrachloride than was the case in hexane. In mixtures of benzene and hexane the trend in E-values followed a linear relationship.

Enzymatic Hydrolysis of Alkyl 3,4-Epoxybutyrates. A New Route to (R)-(-)-Carnitine Chloride

The enzyme-catalyzed hydrolysis of alkyl 3,4-epoxybutyrates to the corresponding epoxy acids is reported.By using esterases the reaction occurred with good stereoselectivity leading to optically active unreacted esters of R configuration.With proteases the stereoselectivity was reversed, and the S enantiomer of the unreacted ester was recovered, albeit in lover enantiomeric excess.Finally, upon preliminary optimization of the reaction conditions, a new synthesis of (R)-(-)-carnitine chloride by the successive use of a stereoselective and of a nonstereoselective enzymatic hydrolysis is shown.

STEREOSELECTIVE SYNTHESIS OF FUNCTIONALIZED ERYTHRO/1,3-DIOLS

V(5+)-Catalyzed t-butylhydroperoxide epoxidation of (Z)-5-hydroxy-2-alkenylsilanes 4 exhibit good to excellent erythro selectivity.The resulting epoxides undergo fragmentation to afford 1,3-diols 8, albeit in low chemical yield.