28968-38-9

Basic information

• Product Name: (R)-2-hydroxymethyl-2-phenylbutanoic acid
• Synonyms: (R)-2-hydroxymethyl-2-phenylbutanoic acid
• CAS NO: 28968-38-9
• Molecular Weight: 194.23
• Mol File: 28968-38-9.mol

Chemical Properties

• CAS DataBase Reference: (R)-2-hydroxymethyl-2-phenylbutanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-hydroxymethyl-2-phenylbutanoic acid(28968-38-9)
• EPA Substance Registry System: (R)-2-hydroxymethyl-2-phenylbutanoic acid(28968-38-9)

Safety Data

• Hazardous Substances Data: 28968-38-9(Hazardous Substances Data)

Upstream product

• 24765-56-8 2-ethyl-2-phenylpropane-1,3-diol 
• 193155-55-4 (S)-2-hydroxymethyl-2-phenylbutyl benzoate 
• 4355-36-6 (+/-)-2-hydroxymethyl-2-phenyl-butyric acid 

Downstream Products

• 88636-87-7 (R)-5-ethyl-5-phenyl-dihydro-[1,3]oxazine-2,4-dione 

Relevant articles and documents

Enzyme-catalyzed asymmetrization of 2,2-disubstituted 1,3-propanediols using 1-ethoxyvinyl esters

The lipase-catalyzed asymmetrization of the prochiral 2,2-disubstituted 1,3-propanediols 1, 6, and 9 was studied using various types of 1-ethoxyvinyl esters 2. Among them, the use of the benzoate 2f provided good chemical and optical yields of the products 3, 7, and 10 bearing chiral quaternary carbon centers which are fairly stable against racemization.

Efficient lipase-catalyzed enantioselective desymmetrization of prochiral 2,2-disubstituted 1,3-propanediols and meso 1,2-diols using 1-ethoxyvinyl 2-furoate

An efficient lipase-catalyzed desymmetrization of prochiral 2,2-disubstituted 1,3-propanediols was developed using 1-ethoxyvinyl 2-furoate 1b, for which the well-known method using vinyl or isopropenyl acetate has had limited success due to low reactivity and easy racemization of the products through acyl group migration. The reagent 1b is highly reactive and converts various prochiral 1,3-diols to the monoesters having a chiral quaternary carbon center with 82-99% ee. These products were stable against racemization under acidic conditions, and their furoyl groups were compatible with oxidative conditions. Prolonging the reaction time led to the kinetic resolution of the monoesters resulting in an increase of their optical purity. The similar desymmetrization of meso cis-1,2-cycloalkanediols gave the monoesters with 82-97% ee without racemization.

1-Ethoxyvinyl 2-furoate, an efficient acyl donor for the lipase-catalyzed enantioselective desymmetrization of prochiral 2,2-disubstituted propane-1,3-diols and meso-1,2-diols

A novel acyl donor, 1-ethoxyvinyl 2-furoate, was found to produce the title reactions with high enantiotopic selectivity, high reactivity and stability of the products under various conditions.

Lipase-catalyzed asymmetric desymmetrization of prochiral 2,2-disubstituted 1,3-propanediols using 1-ethoxyvinyl benzoate

The lipase-catalyzed asymmetric desymmetrization of the prochiral 2,2-disubstituted 1,3-propanediols was studied using various types of 1-ethoxyvinyl esters (1a-i). Although 1a-e with aliphatic acyl groups were not sufficient, use of the benzoate (1f) in combination with Candida rugosa lipases converted acyclic diols (2, 6) and cyclic diols (11-14) to the optically active compounds (3f, 7f, 15f-18f), bearing a quaternary carbon center, with moderate-to-high optical yields. These products were fairly stable against racemization under acidic conditions.