82578-45-8

Basic information

• Product Name: (+)-TERT-BUTYL (S)-3-HYDROXYBUTYRATE
• Synonyms: (S)-3-HYDROXY-BUTYRIC ACID TERT-BUTYL ESTER;(S)-(+)-TERT-BUTYL 3-HYDROXYBUTYRATE;(S)-(+)-T-BUTYL 3-HYDROXYBUTANOATE;(S)-(+)-T-BUTYL 3-HYDROXYBUTYRATE;(+)-TERT-BUTYL (S)-3-HYDROXYBUTYRATE;Butanoic acid, 3-hydroxy-, 1,1-dimethylethyl ester, (3S)-;tert-butyl (3S)-3-hydroxybutanoate;(S)-tert-Butyl 3-hydroxybutanoate
• CAS NO: 82578-45-8
• Molecular Formula: C₈H₁₆O₃
• Molecular Weight: 160.21
• Product Categories: Chiral Building Blocks;Esters;Organic Building Blocks
• Mol File: 82578-45-8.mol
• Article Data: 40

Chemical Properties

• Boiling Point: 228℃
• Flash Point: 87℃
• Appearance: /
• Density: 0.960 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.422
• Storage Temp.: 2-8°C
• PKA: 14.40±0.20(Predicted)
• CAS DataBase Reference: (+)-TERT-BUTYL (S)-3-HYDROXYBUTYRATE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-TERT-BUTYL (S)-3-HYDROXYBUTYRATE(82578-45-8)
• EPA Substance Registry System: (+)-TERT-BUTYL (S)-3-HYDROXYBUTYRATE(82578-45-8)

Safety Data

• Safety Statements: 23-24/25
• Hazardous Substances Data: 82578-45-8(Hazardous Substances Data)

Usage

General Description

(+)-TERT-BUTYL (S)-3-HYDROXYBUTYRATE, also known as (S)-3-Hydroxybutyric acid tert-butyl ester, is a chemical compound that belongs to the class of organic compounds known as beta hydroxy acids and derivatives. It is a colorless liquid with a fruity odor, commonly used in the pharmaceutical and cosmetic industries. (+)-TERT-BUTYL (S)-3-HYDROXYBUTYRATE is often used in the synthesis of pharmaceuticals, and is also used as a flavoring agent in food products. It has a molecular formula of C8H16O3 and a molecular weight of 160.21 g/mol. The compound is derived from (S)-3-hydroxybutyric acid and is commonly used for its antibacterial, antineoplastic, and antiviral properties.

Upstream product

• 1694-31-1 tert-butyl acetoacetate 
• 142176-66-7 (R)-3-Hydroxy-4-((R)-toluene-4-sulfinyl)-butyric acid tert-butyl ester 
• 120444-07-7 (S)-3-Acetoxy-butyric acid tert-butyl ester 
• 108-22-5 Isopropenyl acetate 
• 90435-23-7 tert-butyl 3-hydroxybutyrate 
• 142176-64-5 (+)(R) tert-butyl 3-oxo-4-(p-tolylsulfinyl)butyrate 
• 95112-71-3 (S)-3-Hydroxy-2-methylsulfanyl-butyric acid tert-butyl ester 

Downstream Products

• 101977-76-8 (3S,4R)-3-<(S)-1-hydroxyethyl>-1-p-methoxyphenyl-4-styrylazetidin-2-one 
• 102046-03-7 (3R,4S)-3-<(S)-1-hydroxyethyl>-1-p-methoxyphenyl-4-styrylazetidin-2-one 
• 101977-77-9 <3S,4S(E)>-3-<1(S)-hydroxyethyl>-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone 
• 112020-68-5 (E)-(2S,3R)-2-((S)-1-Hydroxy-ethyl)-3-methoxycarbonylamino-5-phenylsulfanyl-pent-4-enoic acid tert-butyl ester 
• 112020-63-0 (E)-(2S,3S)-2-((S)-1-Hydroxy-ethyl)-3-methoxycarbonylamino-5-phenylsulfanyl-pent-4-enoic acid tert-butyl ester 
• 24621-61-2 1,3-butanediol 
• 220095-33-0 (3S)-3-<<(3'S)-3'-<<(3''S)-3''-<<(3'''S)-3'''-(benzyloxy)butanoyl>oxy>butanoyl>oxy>butanoyl>oxy>butanoic acid tert-butyl ester 
• 220095-38-5 (3S)-3-<<(3'S)-3'-<<(3''S)-3''-<<(3'''R)-3'''-(benzyloxy)butanoyl>oxy>butanoyl>oxy>butanoyl>oxy>butanoic acid tert-butyl ester 
• 220095-34-1 (3S)-3-<<(3'S)-3'-<<(3''R)-3''-<<(3'''R)-3'''-(benzyloxy)butanoyl>oxy>butanoyl>oxy>butanoyl>oxy>butanoic acid tert-butyl ester 
• 220095-36-3 (3S)-3-<<(3'R)-3'-<<(3''R)-3''-<<(3'''R)-3'''-(benzyloxy)butanoyl>oxy>butanoyl>oxy>butanoyl>oxy>butanoic acid tert-butyl ester 
• 220114-14-7 (R,R,R,R,S,S,S,S)-α-benzyl-ω-(tert-butoxy)octakis 
• 220114-13-6 (R,R,R,R,R,S,S,S)-α-benzyl-ω-(tert-butoxy)octakis 
• 220114-12-5 (R,R,R,R,R,R,S,S)-α-benzyl-ω-(tert-butoxy)octakis 
• 220114-11-4 (R,R,R,R,R,R,R,S)-α-benzyl-ω-(tert-butoxy)octakis 

Relevant articles and documents

Effect of organic solvents on asymmetric reduction of β-keto esters using cyanobacterium Synechocystis sp. PCC 6803

The asymmetric reduction of tert-butyl 3-oxobutanoate by cyanobacterium Synechocystis sp. PCC 6803 under illumination with red LED light at 25 °C for 24 h afforded the corresponding (R)-β-hydroxy ester in 79% enantiomeric excess (ee) (81% yield), while the addition of toluene (1% (v/v)) to the system gave the corresponding (S)-β-hydroxy ester in >99% ee (87% yield). Organic solvents such as chloroform, benzene, ethylbenzene, cyclohexane, and methylcyclohexane showed similar effects and afforded the corresponding (S)-β-hydroxy ester in >99% ee. However, polar organic solvents, such as DMSO, THF, and ethanol, as well as dodecane—a hydrophobic solvent with a straight long-chain—did not exhibit such effects.

Chiral BINAP-based hierarchical porous polymers as platforms for efficient heterogeneous asymmetric catalysis

Two vinyl-functionalized chiral 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) ligands, (S)-4,4′-divinyl-BINAP and (S)-5,5′-divinyl-BINAP, were successfully synthesized. Chiral BINAP-based porous organic polymers (POPs), denoted as 4-BINAP@POPs and 5-BINAP@POPs, were efficiently prepared via the copolymerization of vinyl-functionalized BINAP with divinyl benzene under solvothermal conditions. Thorough characterization using nuclear magnetic resonance spectroscopy, thermogravimetric analysis, extended X-ray absorption fine structure analysis, and high-angle annular dark-field scanning transmission electron microscopy, we confirmed that chiral BINAP groups were successfully incorporated into the structure of the materials considered to contain hierarchical pores. Ru was introduced as a catalytic species into the POPs using different synthetic routes. Systematic investigation of the resultant chiral Ru/POP catalysts for heterogeneous asymmetric hydrogenation of β-keto esters revealed their excellent chiral inducibility as well as high activity and stability. Our work thereby paves a path towards the use of advanced hierarchical porous polymers as solid chiral platforms for heterogeneous asymmetric catalysis.

Laboratory scale-up synthesis of chiral carbinols using Rhizopus arrhizus

Rhizopus arrhizus mediated bioreduction was optimized using acetophenone as a model substrate. Various parameters such as bio-processing conditions, reaction time, substrate concentration, temperature, and solvent carrier were studied. This optimized protocol was further exploited for scaled up bioreductions of various prochiral ketones. This study demonstrates the versatility of the fungus Rhizopus arrhizus as a biocatalyst to obtain chiral carbinols in good to excellent yields and selectivities.