289625-33-8

Upstream product

• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 
• 98-88-4 benzoyl chloride 
• 93-56-1 phenylethane 1,2-diol 
• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 
• 501-53-1 benzyl chloroformate 
• 33868-50-7 phenacyl benzoate 

Downstream Products

• 871118-06-8 (R)-[2-(methoxymethoxy)-2-phenyl]ethyl benzoate 
• 871118-07-9 (R)-[2-(acetoxymethoxy)-2-phenyl]ethyl benzoate 
• 499203-35-9 (R)-9-[(2-benzoyloxy-1-phenylethoxy)methyl]guanine 
• 499203-31-5 (R)-1-[(2-benzoyloxy-1-phenylethoxy)methyl]thymine 
• 499203-34-8 (R)-9-[(2-benzoyloxy-1-phenylethoxy)methyl]adenine 
• 499203-33-7 (R)-1-[(2-benzoyloxy-1-phenylethoxy)methyl]cytosine 
• 499203-32-6 (R)-1-[(2-benzoyloxy-1-phenylethoxy)methyl]uracil 

Relevant academic research and scientific papers

Efficient P-Chiral Biaryl Bisphosphorus Ligands for Palladium-Catalyzed Asymmetric Hydrogenation

A series of structurally novel P-chiral biaryl bisphosphorus ligands L1-L5 (BABIBOPs) are developed, providing high efficiency for the first time in palladium-catalyzed asymmetric hydrogenation of β-aryl and β-alkyl substituted β-keto esters. With the Pd-L3 (iPr-BABIBOP) catalyst, a series of chiral β-hydroxyl carboxylic esters are formed in excellent enantioselectivities (up to>99% ee) and yields at catalyst loading as low as 0.01 mol%.

Kinetic Resolution of 1,2-Diols via NHC-Catalyzed Site-Selective Esterification

A kinetic resolution of 1,2-diols bearing both a secondary and a primary alcohol motif through an N-heterocyclic carbene-catalyzed oxidative acylation reaction has been developed. A site- and enantioselective esterification reaction is involved for this process. Both the monoacylated diols obtained and the remaining enantioenriched 1,2-diols are versatile building blocks for the preparation of functional molecules with proven biological activities.

Palladium-catalyzed asymmetric hydrogenation of α-acyloxy-1- arylethanones

First hand: The first example of a palladium-catalyzed asymmetric hydrogenation of α-acyloxy ketones (1) was accomplished to give the hydrogenated products 2 with by far the highest catalytic efficiency in up to quantitative conversions and excellent enantioselectivities. The hydrogenated products could serve as important intermediates for the preparation of many drug candidates. TFE=2,2,2-trifluoroethanol. Copyright

Kinetic resolution of 1,2-diols using nitrogen-tethered bisimidazoline-copper(I) catalyzed benzoylation

Nitrogen-tethered bisimidazoline (Nb-imidazoline) ligand was utilized in the Cu(I)-catalyzed benzoylation of 1,2-diols. With the assistance of i-Pr2NEt, the reaction of rac-1,2-diols with o-methylbenzoyl chloride was smoothly catalyzed by Nb-imidazoline-CuCl in CH2Cl2 to give the corresponding o-methylbenzoylated secondary alcohols in up to 79% ee.

Kinetic resolution of diols and pyridyl alcohols by cu(II)(borabox)- catalyzed acylation

Boron-bridged bisoxazoline (borabox) ligands have been used in the copper(II)-catalyzed benzoylation of pyridyl alcohols and 1,2-diols. Efficient kinetic resolution of 1,2-diols was achieved using both borabox and bisoxazoline (box) ligands. Borabox ligands induced high selectivities in the benzoylation of suitable pyridyl alcohols, where they outperformed bisoxazolines. In addition, highly enantioselective Cu(II)(borabox)-catalyzed benzoylation has been used for the synthesis of both enantiomers of a pyridyl alcohol.

Synthesis, conformation and antiviral activity of nucleoside analogues with the (2-hydroxy-1-phenylethoxy)methyl glycone - A family of nucleoside analogues related to d4T and aciclovir

A complete family of acyclic nucleoside analogues has been obtained by combining the (2-hydroxy-1-phenylethoxy)methyl glycone with the nucleoside bases adenine, guanine, cytosine, thymine and uracil. In each case both optical antipodes have been prepared

Asymmetric synthesis of both enantiomers of two acyclic nucleoside analogues related to d4T and acyclovir

The enantiomers of 1-{[(2-hydroxy-1-phenyl)ethoxy]methyl}thymine and 9-{[(2-hydroxy-1-phenyl)ethoxy]methyl}guanine have been obtained in high yield in five steps from (R)- and (S)-1-phenylethan-1,2-diol. These chiral compounds are acyclic nucleoside analo

Chemo- and stereoselective monobenzoylation of 1,2-diols catalyzed by organotin compounds

A new facile method for monoacylation of diols has been developed. A variety of cyclic and acyclic diols, in particular 1,2-diols, were selectively monobenzoylated in good yields by the reaction with benzoyl chloride in the presence of a catalytic amount of dimethyltin dichloride and inorganic bases such as potassium carbonate. Furthermore, the method was successfully applied to a kinetic resolution of racemic 1-phenyl-1,2- ethanediol using a chiral organotin catalyst. The ee was dependent on the kind of base, water as an additive, and the reaction temperature.

Recent developments in the area of asymmetric transfer hydrogenation

The use of an enantiomerically pure amino alcohol, coupled to a transfer hydrogenation process, in the asymmetric catalysis of the reduction of ketones to alcohols, is described. The process works well for unfunctionalised ketones, affording e.e.s of up to 98%, and excellent conversions. We have recently extended, for the first time in this application, the scope of the methodology to the reductions of α-heteroatom substituted substrates, through the use of the appropriate protecting groups on each atom.

Nonenzymatic kinetic resolution of 1,2-diols catalyzed by an organotin compound

(matrix presented) A new nonenzymatic kinetic resolution method of 1,2-diols 1 using chiral organotin catalyst A with benzoyl chloride was developed. A remarkable effect due to an inorganic base such as sodium carbonate and a small portion of water on the ee of the main products 2 was observed. The reaction showed high enantio-and chemoselectivities to 1,2-diols 1.