68166-83-6

Basic information

• Product Name: (+)-TERT-BUTYL D-LACTATE
• Synonyms: (+)-TERT-BUTYL D-LACTATE;tert-Butyl (R)-(+)-lactate;(+)-tert-Butyl D-lactate >=99.0% (sum of enantiomers, GC);tert-Butyl (2R)-2-hydroxypropanoate;(R)-(+)-Lactic acid tert-butyl ester
• CAS NO: 68166-83-6
• Molecular Formula: C₇H₁₄O₃
• Molecular Weight: 146.18
• Product Categories: Chiral Building Blocks;Esters;Organic Building Blocks
• Mol File: 68166-83-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 38-42 °C
• Boiling Point: 161.821°C at 760 mmHg
• Flash Point: 113 °C
• Appearance: /
• Density: 1.005g/cm³
• Vapor Pressure: 0.77mmHg at 25°C
• Refractive Index: 1.432
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 13.07±0.20(Predicted)
• BRN: 1722069
• CAS DataBase Reference: (+)-TERT-BUTYL D-LACTATE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-TERT-BUTYL D-LACTATE(68166-83-6)
• EPA Substance Registry System: (+)-TERT-BUTYL D-LACTATE(68166-83-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3
• Hazardous Substances Data: 68166-83-6(Hazardous Substances Data)

Usage

Uses

(R)-tert-Butyl 2-hydroxypropanoate is an intermediate used in the stereo controlled synthesis of hydroxy carboxylic acids from L-amino acids.

InChI:InChI=1/C7H14O3/c1-5(8)6(9)10-7(2,3)4/h5,8H,1-4H3/t5-/m1/s1

Upstream product

• 76849-54-2 t-butyl pyruvate 
• 75-65-0 tert-butyl alcohol 
• 111505-48-7 4-Nitro-benzoic acid (R)-1-tert-butoxycarbonyl-ethyl ester 
• 59854-05-6 t-butyl 2(R)-acetoxypropionate 

Downstream Products

• 779331-14-5 2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)phenoxy]-(2S)-propanoic acid 1,1-dimethylethyl ester 
• 419561-56-1 bis[(R)-1-tert-butoxycarbonylethyl] (E)-2,3-dibromobut-2-enedioate 
• 817185-93-6 (R)-2-Benzyloxycarbonylamino-propionic acid (R)-1-tert-butoxycarbonyl-ethyl ester 
• 1053719-19-9 2-{2-{-2{-2(benzyloxy)propanoyloxy}propanoyloxy}propanoyloxy}propanoicacid-tert.butylester 
• 1053719-23-5 2-{2-{-2{-2(benzyloxy)propanoyloxy}propanoyloxy}propanoyloxy}propanoicacid-tert.butylester 
• 1053719-28-0 2-{2-{-2{-2(benzyloxy)propanoyloxy}propanoyloxy}propanoyloxy}propanoicacid-tert.butylester 
• 1053719-31-5 2-{2-{-2{-2(benzyloxy)propanoyloxy}propanoyloxy}propanoyloxy}propanoicacid-tert.butylester 
• 1308257-54-6 (S)-2-((S)-1-tert-butoxycarbonylethylamino)-3-(2',5'-dichlorobiphenyl-4-yl)propionic acid benzyl ester 

Relevant articles and documents

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.

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 ...

Antiglaucoma agents

Pharmaceutical compositions and a method for reducing intraocular pressure by topically applying a carboxyalkyl dipeptide are disclosed.