91510-97-3

Basic information

• Product Name: (-)-(R)-5-pentyl-2(5H)-furanone
• CAS NO: 91510-97-3
• Molecular Weight: 154.209
• Mol File: 91510-97-3.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: (-)-(R)-5-pentyl-2(5H)-furanone(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(R)-5-pentyl-2(5H)-furanone(91510-97-3)
• EPA Substance Registry System: (-)-(R)-5-pentyl-2(5H)-furanone(91510-97-3)

Safety Data

• Hazardous Substances Data: 91510-97-3(Hazardous Substances Data)

Upstream product

• 157497-26-2 (4R,5R)-4,5-dihydro-4-hydroxy-5-pentyl-2-(3H)-furanone 
• 66-25-1 hexanal 
• 246862-25-9 (S)-2-(4-methyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)ethyl 2,4,6-triisopropylphenyl sulfoxide 
• 28163-88-4 (E)-non-3-enoic acid 
• 142-61-0 Hexanoyl chloride 
• 186194-17-2 (4S,5R)-5-pentyl-4-hydroxy-4,5-dihydrofuran-2(3H)-one 
• 124755-24-4 ethyl [bis(2,2,2-trifluoroethoxy)phosphinyl]acetate 
• 133319-86-5 5-((tert-butyldimethylsilyl)oxy)pent-3-yn-2-yl diethyl phosphate 
• 85694-12-8 2,3-O-ethoxymethylene-5-O-toluenesulfonyl-D-ribonolactone 
• 101858-59-7 (R)-1-(Toluene-4-sulfonyl)-heptan-2-ol 
• 101836-35-5 1-((R)-Toluene-4-sulfinyl)-heptan-2-one 
• 123-66-0 Ethyl hexanoate 
• 152442-10-9 (4R,5R)-4,5-dihydro-4-hydroxy-5-iodomethyl-2(3H)-furanone 
• 177608-61-6 (S)-oct-1-yn-3-yl methanesulfonate 

Downstream Products

• 33673-62-0 trans-(4S,5R)-4,5-dihydro-4-methyl-5-pentyl-2(3H)-furanone 
• 63357-96-0 (R)-(+)-γ-nonalactone 

Relevant articles and documents

Organocatalytic sequential α-aminoxylation and cis-Wittig olefination of aldehydes: Synthesis of enantiopure γ-butenolides

A short route to enantiopure γ-butenolides (up to 99% ee) has been developed from readily available starting materials. The strategy involves a sequential organocatalytic α-aminoxylation followed by cis-Wittig olefination of aldehydes. The utility of this protocol has been demonstrated in the asymmetric synthesis of trans-(+)-cognac lactone with high enantiomeric purity.

Enantioselective butenolide preparation for straightforward asymmetric syntheses of γ-lactones - Paraconic acids, avenaciolide, and hydroxylated eleutherol

The naturally occurring γ-lactones (+)-methylenolactocin (13) and its enantiomer, (+)-protolichesterinic acid (14) and its enantiomer, (+)-rocellaric acid (15), and the methylene bis(γ-lactone) (-)-avenaciolide (16) were synthesized with 95-98 % ees in very few steps. Enantiocontrol was imposed by the asymmetric dihydroxylation of trans-configured β,γ-unsaturated carboxylic esters (namely compounds 1i, 1j, and 1n) with AD mix-α [for the levorotatory target structures, except for (-)-avenaciolide] or AD mix-β [for the dextrorotatory target structures plus (-)-avenaciolide]. β,γ-Unsaturated carboxylic ester 1e required increased amounts of the oxidant and auxiliary to produce the hydroxy lactone R,R-3e, a precursor of the naphtho-γ-lactone (+)-9-hydroxyeleutherol (12; 96 % ee). Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

A convergent asymmetric synthesis of γ-butenolides

The addition of aldehydes to the new enantiomerically pure lithiated sulfoxide-orthoester 13 yielded γ-butenolides of high enantiomeric purities after elimination of phenylsulfinic acid. The cyclocondensation with ketones was less stereoselective. This new asymmetric synthesis of γ-butenolides has been applied to a convergent preparation of the antifungal antibiotic (+)-cerulenin.