2404-42-4

Usage

Enantiomer

(R)-1,2-Butanediol, 2-phenyl-

Physical state

Colorless, viscous liquid

Odor

Slightly sweet

Uses

a. Solvent
b. Humectant
c. Chemical intermediate in the production of pharmaceuticals, plasticizers, and food additives
d. Synthesis of chiral auxiliaries
e. Precursor to various other organic compounds

Therapeutic applications

a. Inhibitor of protein kinases
b. Anticonvulsant properties
c. Sedative properties
d. Potential treatment for mood disorders
e. Potential agent for the treatment of addiction and substance abuse

Upstream product

• 89556-33-2 2-<(1'S)-1'-hydroxy-1'-phenylpropyl>hexahydro-4,4,7-trimethyl-4H-1,3-benzoxathiin 
• 69489-15-2 (S)-(-)-hydroxy-2-phenylbutanal 
• 2039-93-2 1-ethylstyrene 
• 636599-74-1 (1S,2R,5R,7S,9R)-5-[(1'S)-1'-hydroxy-1'-phenylpropyl]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane 
• 682352-13-2 (1S,2R,3S,5R,1'S,2'R)-6,6-dimethyl-3-(1'-ethoxy-2'-phenyl-2'-hydroxy-1'-butylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 
• 682352-20-1 (1S,2R,3S,5R,1'R,2'S)-6,6-dimethyl-3-(1'-ethoxy-2'-phenyl-2'-hydroxy-1'-butylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 
• 6175-45-7 2,2-diethoxyacetophenone 
• 682352-08-5 (1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-hydroxymethyl-bicyclo[3.1.1]heptane 
• 682352-09-6 (1S,2R,3S,5R,2'R)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-hydroxymethyl-bicyclo[3.1.1]heptane 
• 682352-10-9 (1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 
• 682352-11-0 (1S,2R,3S,5R,2'R)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 
• 599192-45-7 (1S,2R,5R,7S,9R)-5-benzoyl-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.0^2,7]undecane 
• 266694-57-9 Phenyl-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-methanone 
• 1257246-10-8 4-ethyl-4-phenyl-2-(2-(trifluoromethyl)phenyl)-1,2-oxazetidin-3-one 

Downstream Products

• 2455-52-9 Toluene-4-sulfonic acid (S)-2-hydroxy-2-phenyl-butyl ester 

Relevant academic research and scientific papers

Synthesis of acyldodecaheterocycles derived from (1R)-(-)-myrtenal and evaluation as chiral auxiliaries

New (1R)-(-)-myrtenal-derived macrocycles 5a and 5b were efficiently used as chiral auxiliaries in the diastereoselective nucleophilic addition of several nucleophiles (RMgX, RLi, LiAlH4, and NaBH4). We observed that the diastereosel

A simple primary amine catalyst for enantioselective α-hydroxylations and α-fluorinations of branched aldehydes

A new primary amine catalyst for the asymmetric α-hydroxylation and α-fluorination of α-branched aldehydes is described. The products of the title transformations are generated in excellent yields with high enantioselectivities. Both processes can be performed within short reaction times and on gram scale. The similarity in results obtained in both reactions, combined with computational evidence, implies a common basis for stereoinduction and the possibility of a general catalytic mechanism for α-functionalizations. Promising initial results in α-amination and α-chlorination reactions support this hypothesis.

Resolution of diols via catalytic asymmetric acetalization

A highly enantioselective kinetic resolution of diols via asymmetric acetalization has been achieved using a chiral confined imidodiphosphoric acid catalyst. The reaction is highly efficient for the resolution of tertiary alcohols, giving selectivity factors of up to >300. Remarkably, even in cases where the selectivity factors are only moderate, highly enantioenriched diols are obtained via a stereodivergent resolution to diastereomeric acetals.

Formal [3+2]-cycloaddition of ketenes and oxaziridines catalyzed by chiral lewis bases: Enantioselective synthesis of oxazolin-4-ones

Choose the right cat.: A highly enantioselective synthesis of oxazolin-4-ones by the formal [3+2]-cycloaddition of ketenes and a racemic oxaziridines has been developed (see scheme; cat.=N-heterocyclic carbenes for disubstituted ketenes or cinchona alkaloids for monosubstituted ketenes, Ts=4-toluenesulfonyl).

Catalytic asymmetric dihydroxylation of enamides and application to the total synthesis of (+)-tanikolide

Asymmetric dihydroxylation of β,β- disubstituted enamides afforded chiral tertiary-alcohol-containing α-hydroxyaldehydes and 1,2-diols with high enantioselectivity (see scheme). This method was applied to the total synthesis of the antifungal natural prod

New S,O-acetals from (1R)-(-)-myrtenal as chiral auxiliaries in nucleophilic additions

Treatment of hydroxythiol 4 with α,α-diethoxyacetophenone at room temperature yielded a mixture of epimeric S,O-acetals 6 and 7 (1:4, 92% yield), which were efficiently separated by flash chromatography. The OTBS derivatives 8 and 9 were treated with several Grignard reagents to afford carbinols 10 and 13 respectively (85-99% yield, >95% dr). After successive hydrolysis and reduction of 10 and 13 it is possible to obtain either enantiomer of diols 16 in high optical purity (>95% er).

Enantioselective synthesis of 1-alkyl-substituted 1-phenyl-1,2-ethanediols using a myrtenal-derived chiral auxiliary

The enantioselective synthesis of several 1-phenyl-1,2-ethanodiol derivatives using 2-benzoyl-1,3-oxathiane 1 as a chiral auxiliary is described. Nucleophilic additions of Grignard reagents, methyl lithium and LS-Selectride on benzoyloxathiane 1 proceeded in >95% diastereomeric ratio (dr) affording the corresponding tertiary carbinols, which were successively hydrolyzed and reduced to give the title derivatives in >95% enantiomeric excess (ee).

Camphor-derived 2-stannyl-N-Boc-1,3-oxazolidine: A new chiral formylanion equivalent for the asymmetric synthesis of 1,2-diols

Optically pure 2-tributylstannyl-N-Boc-1,3-oxazolidine 6, prepared from the camphor-derived aminoalcohol 5, was converted to diastereomerically pure 2-acyl derivatives 8 in three steps. Reaction of these ketones with Grignard reaagents at -78°C proceeded with high stereoselectivity affording tertiary carbinols which gave 1,2-diols with >96% ee after hydrolysis and reduction of the intermediate α-hydroxy aldehydes. A new deblocking procedure of the t-Boc group is also described.