71755-17-4

Basic information

• Product Name: methyl β-hydroxy-α-phenylbutyrate
• Synonyms: methyl β-hydroxy-α-phenylbutyrate
• CAS NO: 71755-17-4
• Molecular Weight: 194.23
• Mol File: 71755-17-4.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: methyl β-hydroxy-α-phenylbutyrate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl β-hydroxy-α-phenylbutyrate(71755-17-4)
• EPA Substance Registry System: methyl β-hydroxy-α-phenylbutyrate(71755-17-4)

Safety Data

• Hazardous Substances Data: 71755-17-4(Hazardous Substances Data)

Upstream product

• 75-07-0 acetaldehyde 
• 101-41-7 benzeneacetic acid methyl ester 
• 40195-27-5 (1-methoxy-2-phenylvinyloxy)trimethylsilane 
• 67-56-1 methanol 
• 4374-66-7 rac-(2R,3S)-3-hydroxy-2-phenylbutanoic acid 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 186581-53-3 diazomethane 
• 15082-44-7 dilithium phenyl acetic acid 
• 64-17-5 ethanol 
• 22979-35-7 Methyl phenyldiazoacetate 

Downstream Products

• 121618-64-2 (2S,3S)-3-(tert-butyldimethylsiloxy)-2-phenylbutanal 
• 121618-64-2 erythro-3-(tert-butyldimethylsiloxy)-2-phenylbutanal 

Relevant articles and documents

Synthetic strategies for the synthesis and transformation of substituted pyrrolinones as advanced intermediates for rhazinilam analogues

The biaryl core structure of rhazinilam with its fixed dihedral angle is a pivotal element for its unique in vitro cytotoxic activity. Most of the related natural products are oxidized versions of rhazinilam. Replacing the sensitive pyrrole ring by a pyrrolinone ring is the basis of our initial strategy towards rhazinilam analogues. With this goal, variants of the sequence crossed Mukaiyama aldol reaction followed by the Staudinger reaction were studied. Reacting a suitably substituted acetophenone with O-methyl O-trimethylsilyl ketene acetal gave pyrrolinones 8a and 8b in good to excellent yields. These intermediates could be transformed in four high-yielding steps into the pyrrolic precursors 7a-c containing all the atoms necessary for the construction of rings A, B, and C of rhazinilam. Our studies illustrate a lack of stability of these intermediates. Alternative synthetic approaches towards this central biaryl core structure are described.

Design of α-Alkyl β-Hydroxy Esters Suitable for Providing Optical Resolution by Lipase Hydrolysis

A study of the lipase-catalyzed hydrolyses of various α-substituted β-acetoxy esters revealed that a sulfur functional group in the ester, which could play an important role in the stereorecognition by lipase A6 (Aspergillus sp.) and an anti conformation

Dehydrative Decarboxylation of 2,3-Disubstituted 3-Hydroxycarboxylic Acids with Dimethylformamide Acetals - Mechanistic Studies and Preparative Applicability

Dimethylformamide dimethylacetal (2a) converts the threo-3-hydroxycarboxylic acids 4 smoothly into the (E)/(Z)-olefins 7/6 only if R2 is an aryl or vinyl substituent.Althougt the reaction exhibits a distinct (E)-selectivity it cannot be considered as a stereo-controlled olefin synthesis.If R2 is alkyl, 2a generates the methyl esters 10 from 4.The erythro-acids 5 react with 2a to give 43 - 95percent of >98percent sterically pure 7.As the key tranformation on the multistep way from 4/5 to 6/7 the fragmentation of the zwitterionic intermediate 11/20 is postulated.