63697-00-7

Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

InChI:InChI=1/C6H12O3/c1-4(2)9-6(8)5(3)7/h4-5,7H,1-3H3/t5-/m0/s1

Upstream product

• 923-11-5 isopropyl pyruvate 
• 67-63-0 isopropyl alcohol 
• 26680-10-4 3,6-dimethyl-1,4-dioxane-2,5-dione 
• 4511-42-6 L,L-dilactide 
• 1334227-57-4 (S)-isopropyl 2-acetoxypropanoate 
• 79-33-4 L-Lactic acid 

Downstream Products

• 1383468-48-1 (R)-isopropyl 2-(2-iodophenoxy)propanoate 
• 46755-94-6 (S)-1,1-diphenyl-1,2-propanediol 
• 123054-46-6 (S)-2-(4-Isobutyl-phenyl)-propionic acid (S)-1-isopropoxycarbonyl-ethyl ester 
• 123054-46-6 (R)-2-(4-Isobutyl-phenyl)-propionic acid (S)-1-isopropoxycarbonyl-ethyl ester 
• 146746-19-2 (S)-2-(Toluene-4-sulfonyloxy)-propionic acid isopropyl ester 
• 419561-57-2 bis[(S)-1-isopropoxycarbonylethyl] (E)-2,3-dibromobut-2-enedioate 
• 419561-63-0 bis[(S)-1-isopropoxycarbonylethyl] but-2-ynedioate 
• 1361315-55-0 diisopropyl (2R,2'R)-2,2'-[diselane-1,2-diylbis(2,1-phenyleneoxy)]dipropanoate 
• 1361315-59-4 isopropyl (2R)-2-(2-((2-methoxy-2-phenylethyl)selanyl)phenoxy)propanoate 

Relevant academic research and scientific papers

Preparation method for key intermediate of Barnidipine

he preparation method of the intermediate is characterized by comprising the following steps: with chiral hydroxy acid as a starting material, the chiral hydroxy acid reacts with isopropanol under the catalysis of lewis acid, then reacts with an acetoacetic acid reagent, and is directly cyclized with m-nitrobenzaldehyde and methyl 3-aminocrotonate in an alcohol solvent, then crystallization is performed in a low temperature environment for realizing chiral resolution, hydrolysis is performed by sodium hydroxide, and then acidization is performed by hydrochloric acid to obtain a product. the intermediate is characterized by being prepared by the following steps: with chiral hydroxy acid as a starting material,the chiral hydroxy acid reacts with isopropanol under the catalysis of lewis acid, then reacts with an acetoacetic acid reagent, and is directly cyclized with m-nitrobenzaldehyde and methyl 3-aminocrotonate in an alcohol solvent, crystallization and chiral resolution are realized in a low temperature environment, hydrolysis is performed by sodium hydroxide, and then acidization is performed by hydrochloric acid to obtain a product. The preparation method disclosed by the invention has the advantages that the preparation technology is simple, the resolution is easy, the product yield is high, the optical purity is good, the quality is stable, and the large-scale industrial production is easy.

ANTIVIRAL PRODRUGS OF TENOFOVIR

Compounds of Formula I: and pharmaceutically acceptable salts and co-crystals thereof are useful for the inhibition of HIV reverse transcriptase. The compounds may also be useful for the prophylaxis or treatment of infection by HIV and in the prophylaxis, delay in the onset or progression, and treatment of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antiviral agents, immunomodulators, antibiotics or vaccines.

Preparation method of (R)-(+)-2-p-hydroxyl phenoxyl propionic acid

The invention relates to a preparation method of (R)-(+)-2-p-hydroxyl phenoxyl propionic acid. The method comprises the following steps of taking (S)-(-)-lactic acid as a raw material, and performingthree-step reaction, i.e., esterification, nucleophilic substitution and hydrolysis to obtain a target compound. A synthetic process for the (R)-(+)-2-p-hydroxyl phenoxyl propionic acid is further optimized, and the optimum reaction condition and reagent are screened. According to the preparation method designed in the invention, the reaction steps are shortened, and the yield and optical purity of the (R)-(+)-2-p-hydroxyl phenoxyl propionic acid are improved.

Organosoluble zirconium phosphonate nanocomposites and their supported chiral ruthenium catalysts: The first example of homogenization of inorganic-supported catalyst in asymmetric hydrogenation

In this article, we report the synthesis, structure, morphologies, and asymmetric catalytic properties of a series of novel organosoluble zirconium phosphonate nanocomposites and their supported chiral ruthenium catalysts, which have a good organosolubility (0.1-0.5 g mL-1) in various solvents and mesoporous, filiform, and layered structures. Due to the organosoluble properties in various organic solvents, the first homogenization of zirconium phosphonate-supported catalyst was realized in the field of catalysis. In the asymmetric hydrogenation of substituted α-ketoesters, enantioselectivities (74.3-84.7% ee) and isolated yields (86.7-93.6%) were higher than the corresponding homogeneous Ru(p-cymene)(S-BINAP)Cl2 due to the confinement effect caused by the remaining mesopores in the backbone of the zirconium phosphonate. After completing the reaction, the supported catalyst can be readily recovered in quantitative yield by adding cyclohexane and centrifugation, and reused for five consecutive runs without significant loss in catalytic activity.

Dynamic kinetic resolution of α-substituted β-ketoesters catalyzed by Baeyer-Villiger monooxygenases: Access to enantiopure α-hydroxy esters

BVMOs make a play: The dynamic kinetic resolution of racemic α-alkyl-β-ketoesters was performed through a selective Baeyer-Villiger oxidation employing different Baeyer-Villiger monooxygenases (BVMOs) in mild basic media. The product diesters were obtained with excellent yields and enantioselectivities, and used as precursors for optically active α-hydroxy esters.

Facile alcoholysis of l-lactide catalysed by Group 1 and 2 metal complexes

The application of simple metal amides MN(SiMe3)2 as effective catalysts for the alcoholysis of cyclic esters are demonstrated. Excess dry methanol and L-lactide were added to a Schlenk flask at room temperature (RT) 1 mol% of MN(SiMe3)2, where M = Li, Na or K was added. A blank test was also performed where no catalyst was added giving no reaction. The conversion of M = Li, 45% to methyl (S,S)-lactyllactatewas obtained in 10 minutes at room temperature. Similar behaviors were observed for m = Na and K, where the reactions decelerated after 20 and 30 minutes. The application also extended to other cyclic esters such as capralactone where the ring-opening product was obtained rapidly in quantitative yield.

Synthesis of alkyl (R)-lactates and alkyl (S,S)-O-lactyllactates by alcoholysis of rac-lactide using Novozym 435

Enzymatic alcoholysis of rac-lactide for kinetic resolution was carried out in organic solvents. Effects of organic solvent, reaction temperature, and alcohol as a nucleophile were also investigated in Novozym 435-catalyzed alcoholysis of rac-lactide. Both alkyl (R)-lactate and alkyl (S,S)-O-lactyllactate were simultaneously obtained in high yields (>45%) and high enantiopurities (>97% ee) through Novozym 435-catalyzed ring-opening of rac-lactide and subsequent enantioselective alcoholysis of the resultant alkyl O-lactyllactate.

Enantioselective hydrogenation of pyruvates over polymer-stabilized and supported platinum nanoclusters

The cinchonidine-modified enantioselective hydrogenation of pyruvates has been studied over polyvinylpyrrolidone-stabilized platinum (PVP-Pt) and the corresponding alumina-supported platinum (Al2O3-Pt) clusters. It is shown that the catalysts with particle size less than 2.0 nm demonstrate >90% enantioselectivity in favor of (R)-lactates. The solvent effect is similar to that over the conventional supported platinum catalyst except for tetrahydrofuran. These colloidal and supported clusters are stable with no obvious loss of activity and enantioselectivity even after 18 months standing in air at room temperature. Molecular mechanics calculations of the modifier- reactant interaction on the platinum surface suggest that it is possible to obtain good enantioselectivity on the small clusters.

Chiral Synthesis via Organoboranes. 15. Selective Reductions. 42. Asymmetric Reduction of Representative Prochiral Ketones with Potassium 9-O-(1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl)-9-boratabicyclononane

Potassium 9-O-(1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl)-9-boratabicyclononane (9-O-DIPGF-9-BBNH, K-glucoride), a new stable chiral borohydride reducing agent, was prepared by reaction of the corresponding borinic ester, 9-O-DIPGF-9-BBN, with potassium hydride in THF.The reagent provides high optical induction for asymmetric reduction of prochiral ketones, such as relatively hindered aliphatic ketones, alkyl aromatic ketones, and α-keto esters.In particular, the reduction of hindered α-keto esters provides the corresponding α-hydroxy esters with optical purities approaching 100percent ee.Moreover, the reduction of relatively hindered aliphatic ketones such as 3,3-dimethyl-2-butanone, 2,2-dimethylcyclopentanone, spirononan-1-one, and 2,2-dimethylcyclohexanone yields the corresponding alcohols in 70percent ee, 84percent ee, 82percent ee, and 64percent ee, respectively.The reduction of unhindered aliphatic ketones such as 2-butanone, 3-methyl-2-butanone, 2-octanone, and cyclohexyl methyl ketone provides the corresponding alcohols in relatively low optical purities, 3percent ee, 39percent ee, 27percent ee, and 23percent ee respectively.Alkyl aromatic ketones are reduced to the corresponding alcohols, providing products in 78percent ee for acetophenone, 92percent ee for propiophenone, 87percent ee for butyrophenone, 87percent ee for isobutyrophenone, 85,4percent ee for valerophenone, 97-100percent ee for pivalophenone, and 91percent ee for 2'-methylacetophenone.The reduction of α-keto esters provides the corresponding α-hydroxy esters in exceptionally high ee, such as 86percent ee for methyl pyruvate, 86percent ee for ethyl pyruvate, 87percent ee for isopropyl pyruvate, 81percent ee for tert-butyl pyruvate, 92percent ee for ethyl 2-oxobutanoate, 94percent ee for ethyl 2-oxopentanoate, 98percent ee for methyl 3-methyl-2-oxobutanoate, 97percent ee for ethyl 3-methyl-2-oxobutanoate, 97percent ee for methyl 3,3-dimethyl-2-oxobutanoate, 98percent ee for ethyl 3,3-dimethyl-2-oxobutanoate, 93percent ee for ethyl 4-methyl-2-oxopenyanoate, 92percent ee for methyl benzoylformate, 94percent ee for ethyl benzoylformate, 93percent ee for isopropyl benzoylformate, and 96percent ee for ethyl α-oxo-1-naphthaleneacetate.The reduction of relatively more hindered ketones such as 3,3-diethyl-2-pentanone, 2,2,2-triphenylacetone, 2,2,2-triethylacetophenone, 2,2,2-triphenylacetophenone, and 2',4',6'-trimethylacetophenone results in a serious decrease in optical purity, 25percent ee, 7percent ee, 34percent ee, 4percent ee, and 35percent ee, respectively. 4-Chlorobenzophenone is reduced to 4-chlorobenzhydrol in only 11,5percent ee.Ethyl 2,2-dimethylacetoacetate is reduced to ethyl 2,2-dimethyl-3-hydroxybutanoate in 43percent ee.The reductions of alkyl heterocyclic ketones such as 2-acetylfuran, 2-acetylthiophene, and 3-acetylpyridine afford the corresponding alcohols with 42percent ee, 42percent ee, and 70percent ee, respectively.The reductions of α-halo ketones, 2-chloroacetophenone and 2,2,2-trifluoroacetophenone, yield the corresponding halohydrins in 77percent ee and 48percent ee, respectively. trans-4-Phenyl-3-buten-2-one is reduced to the corresponding allylic alcohol in 60percent ee.The reduction of 4-phenyl-3-butyn-2-one provides the corresponding acetylenic alcohol in 61percent ee.The ...

Selective Reductions. 37. Asymmetric Reduction of Prochiral Ketones with B-(3-Pinanyl)-9-borabicyclononane

The chiral trialkylborane B-(3-pinanyl)-9-borabicyclononane, either with the neat reagents or concentrated solutions, 2 M, reduces a wide range of prochiral carbonyl compounds with good to excellent asymmetric induction.Reduction of simple dialkyl ketones, 2-butanone, 2-octanone, 3-methyl-2-butanone, and 3,3-dimethyl-2-butanone, yields the corresponding alcohols with 43percent, 48percent, 62percent, and 0.7percent asymmetric induction.Acetophenone is reduced to 1-phenylethanol in 85percent ee.The α,β-unsaturated ketones 3-buten-2-one, 1-acetyl-1-cyclohexene, 3-methyl-2-cyclohexenone, and trans-4-phenyl-3-buten-2-one are reduced to the corresponding allylic alcohols with 57percent, 64percent, 11percent, and 97percent asymmetric induction, respecticvely.The α,β-conjugated acetylenic ketones 3-butyn-2-one, 4-methyl-1-pentyn-3-one, and 4-phenyl-3-butyn-2-one underwent a rapid reduction to afford the corresponding propargylic alcohols with 79percent, 99percent, and 91percent enantiomeric purities.The α-haloalkyl aromatic ketones α-chloroacetophenone, α-bromoacetophenone, α-iodoacetophenone, α,p-dibromoacetophenone, α-bromo-p-cyanoacetophenone,α-bromo-2'-acetonaphthone,and α,α,α-trifluoroacetophenone afforded the corresponding halohydrins with 96percent,93percent,93percent,96percent,96percent,90percent,and35percent enantiomeric purities, respectively.The corresponding aliphatic analogue 1-bromo-3-methyl-butanone gave the halohydrin in 66percent ee.The other isomer of this ketone, 3-bromo-3-methyl-2-butanone, failed to undergo reduction.Both the aliphatic and aromatic α-keto esters underwent rapid reduction to give the corresponding α-hydroxy esters with excellentenantiomeric excesses.Thus, methyl, ethyl, isopropyl, and tert-butyl pyruvates afforded the corresponding lactates with 86percent,83percent,78percent, and 92percent ee at 25 deg C,respectively.Lowering the reaction temperature to 0 deg C gave the tert-butyl lactate in 100percent ee.Other aliphatic α-keto esters such as metyl and ethyl 2-oxopentanoates, methyl 3-methyl-2-oxobutanoate, and ethyl 4-methyl-2-oxopentanoate were reduced to the corresponding α-hydroxy esters with 96percent, 96percent, 11percent, and 82percent ee.The methyl, isopropyl, and tert-butyl benzoylformates were reduced to the corresponding mendelic esters with 90percent, 96percent and 100percent ee, respectively.The reduction of the β-keto esters, however, proceeded slowly and ethyl acetoacetate gave the corresponding alcohol with 55percent ee.