283151-79-1

Usage

General Description

1,3-Butanediol, 2-methyl-1-phenyl-, (1R,2S,3S)- is a chiral compound with the chemical formula C11H16O2. It is a colorless liquid with a faint odor, and it is insoluble in water. This chemical is commonly used as a pharmaceutical intermediate and in the production of various types of perfumes and flavorings. It is also utilized as a solvent for various substances and as a chemical intermediate in the manufacturing of other organic compounds. Additionally, it has applications in the production of lubricants and plasticizers. This chemical has a specific stereochemistry, meaning its three-dimensional arrangement of atoms plays a crucial role in its chemical and biological properties.

Upstream product

• 283151-88-2 [3R,4R]-(+)-4-hydroxy-3-methyl-4-phenyl-2-butanone 
• 115936-18-0 (2S,3S)-anti-2-methyl-1-phenyl-3-hydroxy-1-butanone 
• 6668-24-2 2-methyl-1-phenyl-1,3-butanedione 
• 100-52-7 benzaldehyde 
• 219783-11-6 (2R,3R,1'S,2'S)-(+)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-3-phenylpropanamide 
• 74676-21-4 4-hydroxy-3-methyl-4-phenyl-2-butanone 
• 1901-26-4 3-methyl-4-phenyl-3-buten-2-one 

Downstream Products

• 2550-27-8 (2R)-3-methyl-4-phenylbutan-2-one 
• 115936-18-0 (2S,3S)-anti-2-methyl-1-phenyl-3-hydroxy-1-butanone 
• 848413-13-8 (2S,3R)-3-methyl-4-phenyl-2-butanol 

Relevant academic research and scientific papers

Asymmetric Catalytic Enantio- and Diastereoselective Boron Conjugate Addition Reactions of α-Functionalized α,β-Unsaturated Carbonyl Substrates

An efficient catalytic system has been established for the asymmetric boron conjugate addition of B2pin2 onto α-functionalized (involving C, N, O, and Cl) α,β-unsaturated carbonyls under mild, neutral conditions involving Cu[(S)-(R)-ppfa]Cl, AgNTf2, and alcohols. The dual additives of AgNTf2 and alcohols were found to play crucial roles for achieving high catalytic activity and enantio- and diastereoselectivity (up to 98% ee and 70:1 dr).

Baker's yeast reduction of β-hydroxy ketones

Reduction of β-hydroxy ketones to the corresponding 1,3-diols by baker's yeast was investigated, in order to develop methods for simultaneous control over the configurations of multiple stereogenic centres. The reactions were found to be enantiospecific a

A chemo-enzymatic route to diastereoisomers of 2-methyl-1-phenyl-1,3-butanediol: the dual role of microorganisms

Diastereoisomers (1S,2R,3S)-, (1R,2R,3S)-, (1R,2S,3S)- and (1S,2S,3S)-2-methyl-1-phenyl-1,3-butanediols were prepared by simple and convenient strategies using two different chemo-enzymatic approaches for the reduction of racemic 2-methyl-1-phenyl-1,3-but

Asymmetric aldol reactions using (S,S)-(+)-pseudoephedrine-based amides: Stereoselective synthesis of α-methyl-β-hydroxy acids, esters, ketones, and 1,3-syn and 1,3-anti diols

A very efficient method for performing stereoselective aldol reactions is reported. The reaction of (S,S)-(+)-pseudoephedrine-derived propionamide enolates with several aldehydes yielded exclusively one of the four possible diastereomers in good yields, although transmetalation of the firstly generated lithium enolate with a zirconium(II) salt, prior to the addition of the aldehyde, is necessary in order to achieve high syn selectivity. The so-formed syn-α-methyl-β-hydroxy amides were transformed into other valuable chiral nonracemic synthons such as α-methyl-β-hydroxyacids, esters, and ketones. Finally, a stereocontrolled reduction procedure starting from the so-obtained α-methyl-β-hydroxy ketones has been developed allowing the synthesis of either 1,3-syn- or 1,3-anti-α-methyl-1,3-diols in almost enantiopure form by choosing the appropriate reaction conditions.