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
• Article Data: 11

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 
• 254907-27-2 2,2-dimethyl-5-(1-oxohexyl)-1,3-dioxane-4,6-dione 
• 142-61-0 Hexanoyl chloride 
• 10488-95-6 ethyl 3-oxooctanoate 
• 66-25-1 hexanal 
• 59272-25-2 sodium salt of methylsuccinic acid 
• 203514-29-8 (2S,3S,4S)-4-Methyl-5-oxo-2-pentyl-tetrahydro-furan-3-carboxylic acid ethyl ester 
• 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 

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.

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.