133421-02-0

Basic information

• Product Name: erythro-2,2-Dimethyl-5-phenyl-1,3-dioxolan-4-carbonsaeure-ethylester
• Synonyms: erythro-2,2-Dimethyl-5-phenyl-1,3-dioxolan-4-carbonsaeure-ethylester
• CAS NO: 133421-02-0
• Molecular Weight: 250.295
• Mol File: 133421-02-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: erythro-2,2-Dimethyl-5-phenyl-1,3-dioxolan-4-carbonsaeure-ethylester(CAS DataBase Reference)
• NIST Chemistry Reference: erythro-2,2-Dimethyl-5-phenyl-1,3-dioxolan-4-carbonsaeure-ethylester(133421-02-0)
• EPA Substance Registry System: erythro-2,2-Dimethyl-5-phenyl-1,3-dioxolan-4-carbonsaeure-ethylester(133421-02-0)

Safety Data

• Hazardous Substances Data: 133421-02-0(Hazardous Substances Data)

Upstream product

• 77-76-9 2,2-dimethoxy-propane 
• 2272-55-1 ethyl trans-3-phenyl-1-oxirane-2-carboxylate 
• 108741-13-5 (2R,3R)-ethyl 2,3-dihydroxy-3-phenylpropanoate 
• 133421-01-9 3-(Dimethylthexylsiloxy)-3-phenyl-2-(trimethylsiloxy)propannitril 
• 5695-95-4 (R)-2,3-Dihydroxy-3-phenyl-propionic acid 
• 56503-11-8 ethyl (3R)-2,3-dihydroxy-3-phenylpropanoate 
• 67-64-1 acetone 

Downstream Products

• 133520-58-8 [1-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-meth-(Z)-ylidene]-((R)-2-methoxymethyl-pyrrolidin-1-yl)-amine 
• 162600-00-2 ((4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)methanol 

Relevant articles and documents

Gelozymes in organic synthesis. Part IV: Resolution of glycidate esters with crude Mung bean (Phaseolus radiatus) epoxide hydrolase immobilized in gelatin matrix

A crude extract of Mung bean meal (Phaseolus radiatus) possessing epoxide hydrolase activity immobilized in gelatin gel (gelozyme) is employed in the stereoselective epoxide ring opening of glycidate esters. Thus, ethyl trans-(±)-3-phenyl glycidate 1a and methyl trans-(±)-3-(4-methoxyphenyl) glycidate 1b gave (2S,3R)-glycidate esters (ee >99% and 45% yield) with gelatin immobilized enzyme in diisopropyl ether. The corresponding (2R,3S)-enantiomer of 1a was hydrolyzed by an epoxide hydrolase to predominantly give the anti-product, ethyl (2R,3R)-2,3-dihydroxy-3-phenylpropanoate, with a diastereomeric excess of 78% and ee 94% (40%). A small amount (5%) of racemic syn-product was also obtained as a result of the spontaneous hydrolysis. In the case of 1b, the hydrolysis product was racemic due to high reactivity of the glycidate toward water.

Biotransformations with baker's yeast: pH effects on diastereoselectivity during α-hydroxy-β-ketoester reductions and carbon-carbon bond cleavages

Baker's yeast mediated reduction of α-substituted-β-ketoesters lead to reduction of the carbonyl group with high enantiospecificity and diastereoselectivity at low pH (4.0-5.0, e.e. >99%, d.e. >90%) but cleavage of the C-C bond is observed at higher pH >8.0). Similar carbon-carbon bond cleavages are observed in the reactions of α-acetamido-β-ketoesters and acetamidocinnamic acid.