109667-12-1

Basic information

• Product Name: (2S,3S,4S)-4-methyl-5-oxo-2-pentyltetrahydrofuran-3-carboxylic acid
• Synonyms: 3-Furancarboxylic acid, tetrahydro-4-methyl-5-oxo-2-pentyl-, (2S,3S,4S)-
• CAS NO: 109667-12-1
• Molecular Formula: C₁₁H₁₈O₄
• Molecular Weight: 214.2582
• Mol File: 109667-12-1.mol

Chemical Properties

• Boiling Point: 388.6°C at 760 mmHg
• Flash Point: 150°C
• Density: 1.095g/cm³
• Vapor Pressure: 4.05E-07mmHg at 25°C
• Refractive Index: 1.466
• CAS DataBase Reference: (2S,3S,4S)-4-methyl-5-oxo-2-pentyltetrahydrofuran-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4S)-4-methyl-5-oxo-2-pentyltetrahydrofuran-3-carboxylic acid(109667-12-1)
• EPA Substance Registry System: (2S,3S,4S)-4-methyl-5-oxo-2-pentyltetrahydrofuran-3-carboxylic acid(109667-12-1)

Safety Data

• Hazardous Substances Data: 109667-12-1(Hazardous Substances Data)

Upstream product

• 98985-81-0 4-ethoxycarbonyl-4,5-dihydro-3-methyl-5-pentylfuran-2(3H)-one 
• 98985-80-9 diethyl 2-hexanoyl-3-methylsuccinate 
• 142-61-0 Hexanoyl chloride 
• 10488-95-6 ethyl 3-oxooctanoate 
• 66-25-1 hexanal 
• 59272-25-2 sodium salt of methylsuccinic acid 
• 203514-28-7 (2S,3S)-2,3,4,5-tetrahydro-5-oxo-2-pentylfuran-3-carboxylic acid 
• 74-88-4 methyl iodide 
• 807346-06-1 (3S,4S,5S)-4-[(E)-hept-1-enyl]-3-methyl-5-pentyldihydrofuran-2(3H)-one 
• 917590-89-7 (2S,3S,1'S)-2-[1-(tert-butyl-dimethyl-silanyloxy)-hexyl]-3-methylsuccinic acid 1-methyl ester 
• 203514-30-1 (2S,3S,4S)-3-methoxycarbonyl-2-methyl-4-pentyl-γ-butyrolactone 
• 917590-80-8 (2S,3S,1'S)-3-hydroxy-2-(1-phenyl-ethyl)-octanoic acid methyl ester 
• 917590-88-6 (2S,3S,1'S)-3-(tert-butyl-dimethyl-silanyloxy)-2-(1-phenyl-ethyl)-octanoic acid methyl ester 
• 330847-87-5 (6S,7Z,9S)-tetradec-7-ene-6,9-diol 

Relevant articles and documents

A concise synthesis of paraconic acids: (-)-methylenolactocin and (-)-phaseolinic acid

A concise synthesis of (-)-methylenolactocin and (-)-phaseolinic acid, the common members of the paraconic acids, is described. The synthesis is based on regioselective asymmetric dihydroxylation and the orthoester Johnson-Claisen rearrangement of allyl alcohol with a vicinal diol functionality as the key steps. The synthesis was completed in 10 steps with overall yields of 4.1% for (-)-methylenolactocin and 4.3% for (-)-phaseolinic acid.

Stereodivergent Synthesis of Chiral Paraconic Acids via Dynamic Kinetic Resolution of 3-Acylsuccinimides

A direct N-heterocyclic carbene (NHC) catalysis of maleimides with alkyl aldehydes is established for the synthesis of 3-acylsuccinimides. The first dynamic kinetic resolution of 3-acylsuccinimides is accomplished through asymmetric transfer hydrogenation. These two catalytic methodologies are utilized for the synthesis of each enantiomer of trans-paraconic acids in three steps and cis-paraconic acids in four steps with good yields and high stereoselectivities. This stereodivergent synthetic methodology is applied for the synthesis of seven bioactive paraconic acid natural products.

Asymmetric Conjugate Addition of Chiral Secondary Borylalkyl Copper Species

We report the diastereo- and enantioselective conjugate addition of chiral secondary borylalkyl copper species derived from borylalkenes in situ to α,β-unsaturated diesters. In the presence of a chiral bisphosphine-ligated CuH catalyst, the conjugate addition provides a direct access to enantioenriched alkylboron compounds containing two contiguous carbon stereogenic centers in good yield with high diastereo- and enantioselectivity (up to >98:2 dr, >99:1 er) by assembling readily available starting alkenyl reagents in a single operation without using preformed organometallic reagents or chiral auxiliaries. The resulting products were used in various organic transformations. The utility of the synthetic approach was highlighted by the synthesis of (?)-phaseolinic acid.

Concise syntheses of (+)- and (-)-methylenolactocins and phaseolinic acids

(+)- and (-)-Methylenolactocins and phaseolinic acids are synthesized in four steps via asymmetric syn- and anti-aldol reactions of chiral N-succinyl-2-oxazolidinones using the same set of reagents.

General enantioselective synthesis of butyrolactone natural products via ruthenium-SYNPHOS-catalyzed hydrogenation reactions

Enantioselective syntheses of several paraconic acids have been achieved using catalyzed asymmetric hydrogenation of β-keto esters with SYNPHOS as a ligand. This strategy allowed the short synthesis of biologically active (-)-methylenolactocin 1, (-)-protolichesterinic acid 2, (-)-phaseolinic acid 3 and (+)-roccellaric acid 4.

Catalytic asymmetric synthesis of acyclic arrays by tandem 1,4-addition-aldol reactions

Herein, we report efficient acyclic stereocontrol in tandem 1,4-addition-aldol reactions triggered by catalytic asymmetric organometallic addition. Grignard reagents add to α,β-unsaturated thioesters in a 1,4-fashion and the resulting magnesium enolates are trapped with aromatic or aliphatic aldehydes. The process provides a range of tandem products bearing three contiguous stereocenters with excellent control of relative and absolute stereochemistry. The various diastereomeric products have been fully characterized using single-crystal X-ray analysis and the origins of stereocontrol in this tandem protocol are discussed. The versatility and efficiency of this methodology are demonstrated in the first catalytic asymmetric synthesis of (-)-phaseolinic acid with 54% overall yield via a short and concise route.

A versatile stereoselective approach to paraconic acids

A versatile methodology has been developed for the independent stereochemical control in the construction of all the stereocenters of the γ-butyrolactone skeleton that are present in paraconic acids (1 and 2). The configuration of the γ-carbon came from an enantiopure alk-2-yne-1,4-diol. Stereoselective partial reduction to a (Z)- or (E)-alk-2-ene-1,4-diol (10) controlled the stereochemistry of the β-carbon whereas the α-carbon stereochemistry in 1 was partially selected by a (Z)- or (E)-enolate formation of the 1,4-dipropanoate derived from diol (10).

A straightforward synthesis of (-)-phaseolinic acid

A concise approach to (-)-phaseolinic acid starting from commercially available (S)-oct-1-yn-3-ol is disclosed. The key steps are a ring-closing metathesis reaction to prepare a C2-symmetrical allylic diol and its desymmetrization to a γ-butyrolactone by using an Ireland-Claisen rearrangement. The 2S,3S,4S configuration of the levogyre natural product has been confirmed.

Enantioselective syntheses of (+)- and (-)-phaseolinic acid

(+)- and (-)-Phaseolinic acid (1) have been prepared in an enantioselective fashion from acetylenic acid 26 (or ent-26) by a three step sequence involving lactonization, epimerization at C3, and oxidative cleavage. 26 was obtained as a single enantiomer using a Nicholas-Schreiber reaction.