66997-70-4

Usage

Uses

Used in Flavor and Fragrance Industry:
(S)methyl 3-hydroxyhexanoate is used as a key component in the creation of flavors and fragrances due to its distinctive fruity and sweet scent. This application takes advantage of the compound's natural aroma to enhance the sensory experience of various products.
Used in Pharmaceutical Synthesis:
As a raw material, (S)methyl 3-hydroxyhexanoate plays a crucial role in the synthesis of pharmaceuticals. Its chemical properties make it a suitable candidate for the development of new drugs and medicinal compounds, contributing to advancements in healthcare.
Used in Solvent Applications:
(S)methyl 3-hydroxyhexanoate serves as an effective solvent in various chemical processes. Its ability to dissolve other substances makes it a valuable asset in the production and manufacturing of different products, particularly in the chemical and industrial sectors.
Used in Biotechnology:
(S)methyl 3-hydroxyhexanoate has potential applications in the field of biotechnology. Its unique properties may be harnessed for various purposes, such as enhancing biological processes or developing innovative solutions for complex biological challenges.
Used in Agriculture:
In agriculture, (S)methyl 3-hydroxyhexanoate may find use in the development of new products or techniques that can improve crop yield, pest control, or other agricultural practices. Its potential applications in this field highlight the compound's versatility and its ability to contribute to a wide range of industries.

Upstream product

• 186581-53-3 diazomethane 
• 66997-60-2 (+)-(3S)-3-hydroxyhexanoic acid 
• 108082-41-3 (2R,3S)-3-Hydroxy-2-phenylsulfanyl-hexanoic acid methyl ester 
• 67-56-1 methanol 
• 505-57-7 2-hexenal 
• 141339-40-4 S-1-chloromethyl-1-butanol 
• 108082-37-7 (R)-3-((2R,3S)-3-Hydroxy-2-phenylsulfanyl-hexanoyl)-2-thioxo-thiazolidine-4-carboxylic acid methyl ester 
• 87319-85-5 (1'R,3S)-3-Hydroxy-N-(2-hydroxy-1-phenylethyl)-hexanamid 
• 95061-50-0 (1'R,3S)-3-Hydroxyhexansaeure-(2-hydroxy-1,2,2-triphenylethyl)ester 
• 109053-79-4 (Z)-(S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(dimethyl-phenyl-silanyl)-hex-4-en-1-one 
• 30414-54-1 methyl 3-oxohexanoate 
• 109053-83-0 (R)-3-(Dimethyl-phenyl-silanyl)-hexanoic acid methyl ester 
• 17430-98-7 [(1S)-1-cyclohexylethyl]amine 

Downstream Products

• 67217-85-0 (-)-indolizidine 223AB 
• 143617-62-3 (S)-toluene-4-sulfonic acid 3-hydroxy-hexyl ester 
• 1016225-14-1 (S)-3-hydroxy-N-phenylhexanamide 
• 1017238-03-7 methyl (3S)-3-{[tert-butyl(diphenyl)silyl]oxy}hexanoate 
• 774216-23-8 methyl (R)-3-(phenylamino)hexanoate 

Relevant academic research and scientific papers

Enantioselective reduction of β-keto esters

Highly enantioselective reduction of β-keto esters with BINAP-Ru catalyst can be effected at 50 psig H2 and 80°, using a Parr shaker. A simplified preparation of the BINAP·Ru catalyst is reported.

Brivaracetam chiral intermediate and preparing method thereof

The invention relates to an antiepileptic drug brivaracetam chiral intermediate and a preparing method thereof. The preparing method of a compound, shown in a formula 1, of the brivaracetam chiral intermediate comprises the steps of with S-epichlorohydrin (a compound shown in a formula 7 being an original raw material, conducting open-loop preparing on ethyl metal reagent under the effect of Lewisacid to obtain a compound shown in a formula 6; conducting preparing on the compound shown in the formula 6 in the presence of a metal catalyst through a substitution reaction to obtain a compound shown in a formula 5; conducting cyan alcoholysis on the compound shown in the formula 5 under the effect of acid to obtain a compound shown in a formula 4; preparing the compound shown in the formula 4through the effect of hydroxyl activity reagent to obtain a compound shown in a formula 3; conducting preparing on the compound shown in the formula 3 and nitromethane through an SN2 nucleophilic substitution effect to obtain a compound shown in a formula 2; conducting cyclization preparing on the compound shown in the formula 2 through the effect of concentrated sulfuric acid and an Nef reactionto obtain a compound shown in a formula 1, namely the brivaracetam chiral intermediate. By means of the preparing method, the compound high in optical purity and shown in the formula 1 can be prepared and solve the problem that currently produced brivaracetam needs complex unit operation high in cost like a column chromatography and a chiral preparation column.

N-heterocyclic carbene-catalyzed radical reactions for highly enantioselective β-hydroxylation of enals

An N-heterocyclic carbene-catalyzed β-hydroxylation of enals is developed. The reaction goes through a pathway involving multiple radical intermediates, as supported by experimental observations. This oxidative single-electron-transfer reaction allows for highly enantioselective access to β-hydroxyl esters that are widely found in natural products and bioactive molecules.

Chiral Surfactant-Type Catalyst: Enantioselective Reduction of Long-Chain Aliphatic Ketoesters in Water

A series of amphiphilic ligands were designed and synthesized. The rhodium complexes with the ligands were applied to the asymmetric transfer hydrogenation of broad range of long-chained aliphatic ketoesters in neat water. Quantitative conversion and excellent enantioselectivity (up to 99% ee) was observed for α-, β-, γ-, δ- and ε-ketoesters as well as for α- and β-acyloxyketone using chiral surfactant-type catalyst 2. The CH/π interaction and the strong hydrophobic interaction of long aliphatic chains between the catalyst and the substrate in the metallomicelle core played a key role in the catalytic transition state. Synergistic effects between the metal-catalyzed site and the hydrophobic microenvironment of the core in the micelle contributed to high stereoselectivity. (Chemical Equation Presented).

Enzymatic total synthesis of banana volatile (S)-2-pentyl (R)-3-hydroxyhexanoate

The banana volatile (S)-2-pentyl (R)-3-hydroxyhexanoate has been synthesized in 79 % yield and high optical purity (>99 % ee, >99 % de) starting from methyl 3-oxohexanoate and 2-pentanone. The synthetic method consists of three steps and the key reactions are enzymatic reduction and enzymatic transesterification. Copyright

Formal total synthesis of neopeltolide

A concise synthesis of the core structure of the macrolide neopeltolide was develop featuring a Prins cyclization to fashion the pyran ring. Key steps in the synthesis of aldehyde 16 were a Leiqhton allylation and a Feringa-Minnaard asymmetric methyl cuprate addition to an unsaturated thioester. For lactonization, a classical Yamaguchin macrolactonization was used. The longest linear sequence consists of 17 steps providing lactone 26 with an overall yield of 23%.

Efficient amide-directed catalytic asymmetric hydroboration

A series of acyclic β,γ-unsaturated amides are shown to undergo highly regio- (>95%) and enantioselective (93-99% ee) rhodium-catalyzed hydroboration with pinacolborane (PinBH) using simple chiral monophosphite or phosphoramidite ligands in combination wi

Over 98% optical yield achieved by a heterogeneous catalysis. Substrate design and analysis of enantio-differentiating factors of tartaric acid-modified Raney nickel hydrogenation

Tartaric acid-modified Raney nickel (TA-MRNi) is a chiral heterogeneous catalyst for the hydrogenation of prochiral ketones. An optical yield (OY) of 86% with methyl acetoacetate (1) as a substrate was improved to 94-96% by employing β-keto esters having a proper bulkiness at the γ-position. The γ-bulkiness effect contributes to a high intrinsic enantio-differentiating ability (factor-i) of the TA-MRNi catalysis. Through the study, we found the best substrate, γ-cyclopropyl-β-keto ester, the hydrogenation of which resulted in 98.6% OY. This further improvement in the OY was ascribed to a smaller contribution of non-enantio-differentiating hydrogenation (N-site catalysis) due to the substrate-specific activation of the enantio-differentiating hydrogenation by the chiral modifier. The OY of the hydrogenation of 1 was analyzed by comparing with well-behaved β-keto esters, and the contribution of the factor-i and the N-site to the OY value was evaluated to deduce the origin of the enantiodifferentiation.

Efficient enantioselective synthesis of methyl esters of α-unsubstituted β-hydroxy acids via asymmetric aldol-type addition of chiral boron enolates of (methylthio)acetic acid to aldehydes

The aldol-type addition of chiral boron enolates of (methylthio)acetic acid to various aldehydes gives α-(methylthio)-β-hydroxy acids stereoselectively and with good yields. The desulfenylation of methyl esters of the condensation adducts allows methyl es

Enantioselective Ru-Mediated Synthesis of (-)-Indolizidine 223AB

Triphenylphosphine/CCl4-mediated cyclization of amino alcohol 17 proceeded smoothly, with single inversion, to provide (-)-indolizidine 223AB 4.Amino alcohol 17 was prepared by thermolysis of azide 16, followed by DIBAL reduction of the intermediate imine.Symchiral aldehyde 12 and phosphonium salt 15, precursors to 16, were prepared by BINAp*Ru*-mediated hydrogenation of the corresponding β-Keto esters.A simplified procedure allows this hydrogenation to be carried out in a Parr shaker, at 80 deg C and 50 psig of H2.