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

Description

(+)-TERT-BUTYL D-LACTATE, also known as (R)-tert-Butyl 2-hydroxypropanoate, is a chiral compound that serves as an important intermediate in the synthesis of various organic compounds. It is a derivative of D-lactate, featuring a tert-butyl group attached to the hydroxyl group, which provides unique reactivity and selectivity in chemical reactions.
Used in Pharmaceutical Industry:
(+)-TERT-BUTYL D-LACTATE is used as a chiral building block for the enantioselective synthesis of pharmaceuticals and biologically active molecules. Its unique stereochemistry allows for the creation of specific drug candidates with desired properties, such as improved efficacy, selectivity, and reduced side effects.
Used in Chemical Synthesis:
(+)-TERT-BUTYL D-LACTATE is used as a versatile intermediate in the stereo-controlled synthesis of hydroxy carboxylic acids from L-amino acids. This application is crucial for the development of complex organic molecules and the production of enantiomerically pure compounds, which are essential in various fields, including pharmaceuticals, agrochemicals, and materials science.
Used in Research and Development:
(+)-TERT-BUTYL D-LACTATE is utilized as a valuable research tool in the study of asymmetric catalysis, organocatalysis, and other advanced synthetic methodologies. Its unique reactivity and stereochemistry enable the exploration of new reaction pathways and the development of innovative synthetic strategies for the preparation of enantiomerically pure compounds.

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

Downstream Products

• 174966-18-8 benzyloxycarbonyl L-phenylalanyl D-lactic acid t-butyl ester 
• 174743-68-1 O-acetyl-N-benzyloxycarbonyl L-tyrosyl D-lactic acid t-butyl ester 
• 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 
• 671792-64-6 tert-butyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-glucopyranosyl)-D-lactate 
• 671792-61-3 tert-butyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-glucopyranosyl)-D-lactate 
• 817185-93-6 (R)-2-Benzyloxycarbonylamino-propionic acid (R)-1-tert-butoxycarbonyl-ethyl ester 
• 671792-66-8 tert-butyl O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-D-lactate 
• 476689-68-6 tert-butyl (2R)-2-({(2E)-2-[(4-methoxyphenyl)imino]ethanoyl}oxy)propanoate 
• 476689-66-4 tert-butyl-(2R)-2-({(2E)-2-[(5-chloro-2-iodophenyl)imino]ethanoyl}oxy)propanoate 
• 476689-69-7 (1R)-tert-butoxy-1-methyl-2-oxoethyl (2R)-2-(4-methoxyanilino)-4-pentenoate 
• 476689-71-1 (1R)-tert-butoxy-1-methyl-2-oxoethyl (2R)-2-(4-methoxyanilino)pentanoate 
• 252349-38-5 (1R)-2-tert-butoxy-1-methyl-2-oxoethyl (2R)-2-(5-chloro-2-iodoanilino)-4-oxobutanoate 
• 476689-67-5 (1R)-2-(tert-butoxy)-1-methyl-2-oxoethyl (2R)-2-(5-chloro-2-iodoanilino)-4-pentenoate 

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.

BIOCATALYTIC RESOLUTION OF (+/-)-HYDROXYALKANOIC ESTERS. A STRATEGY FOR ENHANCING THE ENANTIOMERIC SPECIFICITY OF LIPASE-CATALYZED ESTER HYDROLYSIS.

A general biocatalytic procedure for the preparation of a variety of R- and S-hydroalkanoic esters of high optical purity has been developed.The noteworthy feature of this methodology resides in the selection of a nonhydrolyzable ester at the carboxyl terminus to improve the enantiospecificity in the lipase-catalyzed hydrolysis of the acyloxy ester.

Antiglaucoma agents

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