146235-25-8

Basic information

• Product Name: (2R)-2-acetoxy-3-phenylpropanoic acid
• Synonyms: (2R)-2-acetoxy-3-phenylpropanoic acid
• CAS NO: 146235-25-8
• Molecular Weight: 208.214
• Mol File: 146235-25-8.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (2R)-2-acetoxy-3-phenylpropanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2-acetoxy-3-phenylpropanoic acid(146235-25-8)
• EPA Substance Registry System: (2R)-2-acetoxy-3-phenylpropanoic acid(146235-25-8)

Safety Data

• Hazardous Substances Data: 146235-25-8(Hazardous Substances Data)

Upstream product

• 673-06-3 D-(R)-phenylalanine 
• 64-19-7 acetic acid 
• 5801-58-1 α-acetoxy-cinnamic acid 
• 828-01-3 phenyllactic acid 
• 69056-25-3 (RS)-2-acetyloxy-3-phenyl propanoic acid 
• 828-01-3 D-phenyllactic acid 
• 108-24-7 acetic anhydride 
• 108-05-4 vinyl acetate 

Downstream Products

• 1240521-70-3 (R)-1-fluoro-1-oxo-3-phenylpropan-2-yl acetate 
• 1240522-34-2 (R)-1-(1-ethyl-3-(pyridine-4-yl)-1H-pyrazol-ylamino)-1-oxo-3-phenylpropan-2-yl acetate 
• 1316671-14-3 C₃₄H₃₇NO₆ 
• 1316671-16-5 (R)-N-(9-fluorenylmethoxycarbonyl)-(S)-pipecolinylphenyllactic acid 
• 111505-52-3 D-α-hydroxyhydrocinnamic acid t-butyl ester 
• 159990-95-1 3-phenyl-2(R)-acetoxypropionic acid t-butyl ester 
• 27000-00-6 methyl 2-hydroxy-3-phenylpropionate 
• 701261-90-7 methyl (R)-2-(methoxymethoxy)-3-phenylpropanoate 

Relevant articles and documents

Trichosporon cutaneum-promoted deracemization of (±)-2-hydroxindan-1-one: a mechanistic study

A mechanistic study of the deracemization of (±)-2-hydroxy-1-indanone mediated by the yeast Trichosporon cutaneum to afford pure (1S,2R)-1,2-indandiol is reported. The key aspect of the study was the use of pure (R)- and (S)-2-hydroxy-1-indanone enantiomers to ensure reliable conclusions. Experiments in the absence of yeast cells or using dead cells disclosed that the pure enantiomers were not racemized, which suggest that the whole dynamic kinetic resolution process is enzymatic in character. When living yeast cells were used the (R)-substrate was smoothly converted to (1S,2R)-1,2-indandiol, whilst the (S)-2-hydroxy-1-indanone was converted to the same diol through a more complex fashion, which requires a more lengthy oxidation-reduction pathway having the 1,2-indanedione as an achiral intermediate. An unexpected observation was that 1,2-indanone acts as a moderate inhibitor of the reductive enzymes acting in the conversion of (R)-2-hydroxy-1-indanone to (1S,2R)-1,2-indandiol.

Total Synthesis of (+)-Prunustatin A: Utility of Organotrifluoroborate-Mediated Prenylation and Shiina MNBA Esterification and Macrolactonization to Avoid a Competing Thorpe-Ingold Effect Accelerated Transesterification

A convergent total synthesis of (+)-prunustatin A is described through the assembly of two key fragments and a macrolactonization. Shiina MNBA couplings were used for the formation of each of the four ester bonds in the tetralactone ring, including the key macrocyclization which was essential to minimize competing Thorpe-Ingold accelerated transesterification. Other key steps included an organoboron-based prenylation using potassium prenyltrifluoroborate and a carbonyldiimidazole-mediated coupling to form the salicylamide.

Total synthesis of the antifungal depsipeptide petriellin A

We report the solid-phase total synthesis of the antifungal highly modified cyclic depsipeptide petriellin A. The synthesis confirms earlier reports on the absolute configuration of the natural product. The solid-phase approach resulted in a protected lin