189098-10-0

Basic information

• Product Name: ethyl (2R,3R)-3-phenyl-3-hydroxy-2-methylpropionate
• Synonyms: ethyl (2R,3R)-3-phenyl-3-hydroxy-2-methylpropionate
• CAS NO: 189098-10-0
• Molecular Weight: 208.257
• Mol File: 189098-10-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: ethyl (2R,3R)-3-phenyl-3-hydroxy-2-methylpropionate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (2R,3R)-3-phenyl-3-hydroxy-2-methylpropionate(189098-10-0)
• EPA Substance Registry System: ethyl (2R,3R)-3-phenyl-3-hydroxy-2-methylpropionate(189098-10-0)

Safety Data

• Hazardous Substances Data: 189098-10-0(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 189098-09-7 (2S)ethyl N-[2R,3R-(3-hydroxy-2-methyl-3-phenylpropionyl)]-4,4-dimethylpyroglutamate 
• 652150-85-1 (3R,4R)-3-methyl-4-phenyloxetan-2-one 
• 10488-87-6 ethyl 2-benzoylpropionate 
• 100-52-7 benzaldehyde 
• 140-88-5 ethyl acrylate 
• 73967-97-2 (1E)-1-ethoxy-1-(trimethylsiloxy)propene 

Downstream Products

• 76549-04-7 (2R,3R)-(+)-3-hydroxy-2-methyl-3-phenylpropanoic acid 

Relevant articles and documents

Cinchona Alkaloid-Lewis Acid Catalyst Systems for Enantioselective Ketene-Aldehyde Cycloadditions

Asymmetric cinchona alkaloid-catalyzed acid chloride-aldehyde cyclocondensation (AAC) reactions afford enantioenriched 4-substituted and 3,4-disubstituted β-lactones with near perfect absolute and relative stereocontrol. These reactions are characterized

Diastereoselective radical debromination approach toward divergent syntheses of syn- and anti-propionate units, coupled with enantioselective and/or diastereoselective Lewis acid-promoted aldol reactions

A practical methodology directed to the enantioselective synthesis of polypropionate backbones, available for the synthesis of polyketide natural products, has been developed by iterative enantio- and diastereoselective Lewis acid-promoted aldol reactions, followed by diastereoselective radical debromination reactions. A chiral oxazaborolidinone-promoted aldol reaction of a racemic aldehyde, derived from 2-methyl-1,3-propanediol, with a silylketene acetal from ethyl 2-bromopropionate, resulted in highly enantioselective formation of the corresponding bromo aldol adduct, followed by radical debromination with Bu3SnH in the presence of Et3B to divergently give syn- and anti-propionate aldols, which are versatile stereotriads. Furthermore, elongation of the propionate units has also been achieved: the BF3·OEt2-promoted aldol reaction of chiral syn- and anti-α-methyl-β-protected-oxy aldehydes with the silyl nucleophile proceeded with essentially complete syn-selectivity while the TiCl4-promoted aldol reaction resulted in fairly good anti-selectivity. The resulting bromo aldol adducts were divergently debrominated by the radical reduction to give a complete set of stereotetrads.

Enantioselective aldol reaction using bornane-2,3-diol-aluminum complex as a chiral Lewis acid

β-Hydroxy ester was formed in high enantiomeric excess by the reaction of ketene silyl acetal with aldehyde in the presence of a chiral Lewis acid prepared from diethylaluminum chloride and chiral diol derived from (+)-camphor.