128301-15-5

Basic information

• Product Name: methyl (2R,3S)-2-phenyl-3-hydroxybutanoate
• Synonyms: methyl (2R,3S)-2-phenyl-3-hydroxybutanoate
• CAS NO: 128301-15-5
• Molecular Weight: 194.23
• Mol File: 128301-15-5.mol

Chemical Properties

• CAS DataBase Reference: methyl (2R,3S)-2-phenyl-3-hydroxybutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2R,3S)-2-phenyl-3-hydroxybutanoate(128301-15-5)
• EPA Substance Registry System: methyl (2R,3S)-2-phenyl-3-hydroxybutanoate(128301-15-5)

Safety Data

• Hazardous Substances Data: 128301-15-5(Hazardous Substances Data)

Upstream product

• 75-07-0 acetaldehyde 
• 101-41-7 benzeneacetic acid methyl ester 
• 4374-66-7 rac-(2R,3S)-3-hydroxy-2-phenylbutanoic acid 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 67-56-1 methanol 
• 186581-53-3 diazomethane 
• 15082-44-7 dilithium phenyl acetic acid 

Downstream Products

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

Relevant articles and documents

Asymmetric catalytic C-H activation applied to the synthesis of syn-aldol products

(formula presented) Rh2(R-DOSP)4-catalyzed decomposition of methyl phenyldiazoacetate in the presence of tetraalkoxysilanes results in the asymmetric synthesis of syn-aldol products. This catalytic asymmetric intermolecular C-H activ

Organoaluminum-catalyzed rearrangement of epoxides a facile route to the synthesis of optically active β-siloxy aldehydes

A new, stereocontrolled rearrangement of epoxy silyl ethers leading to β-siloxy aldehydes has been effected with stoichiometric use of exceptionally bulky, oxygenophilic methylaluminum bis(4-bromo-2,6-di-trert-butylphenoxide) (MABR) under mild conditions. Used in combination with the Sharpless asymmetric epoxidation of allylic alcohols, this rearrangement represents a new approach to the synthesis of various optically active β-hydroxy aldehydes, useful intermediates in natural product synthesis. The modified organoaluminum reagent, MABR is also applicable to the transformation of a variety of simple epoxides to carbonyl compounds with high efficiency and selectivity. Further, the catalytic version for the rearrangement of epoxy silyl ethers as well as simple epoxides has been newly devised. The scope and limitation of this catalytic method has been clarified with various epoxy substrates.

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

Enantioselective Diastereospecific Synthesis of anti-α-Alkyl-β-hydroxy Esters through Cuprate Opening of Glycidic Esters

A diastereospecific chain elongation of the aldehydes 1 to anti-αalkyl-β-hydroxy esters 2 via the intermediates 4 - 7 is described.By means of the Sharpless epoxidation, 2 may be obtained with >90percent ee in either enantiomer.

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.