56279-37-9

Upstream product

• 108-29-2 5-methyl-dihydro-furan-2-one 
• 112789-84-1 (+)-(S)-ethyl 4-hydroxypentanoate 
• 13532-37-1 4-hydroxyvaleric acid 

Downstream Products

• 19041-15-7 (S)-γ-valerolactone 
• 952745-68-5 ethyl 2-[6-(1,3-dithiane)undec-10-enyl] (4,6-diisopropoxy-2-vinylphenyl)phosphonate 

Relevant academic research and scientific papers

Stability of gamma-valerolactone under neutral, acidic, and basic conditions

Dry gamma-valerolactone (GVL) is stable for several weeks at 150?°C and its thermal decomposition only proceeds in the presence of appropriate catalysts. Since GVL does not react with water up to 60?°C for several weeks, it could be used as a green solvent at mild conditions. At higher temperatures, GVL reacts with water to form 4-hydroxyvaleric acid (4-HVA) and reaches the equilibrium in a few days at 100?°C. Aqueous solutions of acids (HCl and H2SO4) catalyze the ring opening of GVL even at room temperature, which leads to the establishment of an equilibrium between GVL, water, and 4-HVA. Although the 4-HVA concentration would be below 4?mol% in the presence of acids, it could be higher than the concentration of a reagent or a catalyst precursor, not to mention a catalytically active species. The latter could be especially worrisome as 4-HVA could be an excellent bi- or even a tri-dentate ligand for transition metals. Aqueous solution of bases (NaOH and NH4OH) also catalyzes the reversible ring opening of GVL. While in the case of NaOH, the product is the sodium salt of 4-hydroxyvalerate, the reversible reaction of GVL, with NH4OH results in the formation of 4-hydroxyvaleric amide. The reversible ring opening of (S)-GVL in the presence of HCl or NaOH has no effect on the stability of the chiral center.

Mild and chemoselective lactone ring-opening with (TMS)ONa. Mechanistic studies and application to sweroside derivatives

Mild and chemoselective opening of lactones with sodium trimethylsilanolate in high yields and aprotic solvents is described. Kinetic studies demonstrate that the BAc2 mechanistic pathway is followed. Nucleophilic attack of silanolate onto the carbonyl of the lactone moiety is the rate-determining step. NaOH present as an impurity accelerates the reaction. The method was further applied to the base-sensitive and stable lactones derived from highly functionalized iridoid derivatives.

Synthetic and computational studies on the tricarboxylate core of 6,7-dideoxysqualestatin H5 involving a carbonyl ylide cycloaddition- rearrangement

Reaction of diazodiketoesters 17 and 28 with methyl glyoxylate in the presence of catalytic rhodium(ii) acetate generates predominantly the 6,8-dioxabicyclo[3.2.1]octanes 29 and 30, respectively. Acid-catalysed rearrangement of the corresponding alcohol 3

Synthesis of a transition-state analog for the hydrolysis of the zearalenone lactone

The development of a catalytic antibody for the hydrolysis of the lactone functionality in zearalenone (1) is viewed as a potential solution to animal fertility problems associated with the estrogenic mycotoxin. A phosphonomacrolactone is proposed as a ha

4-SUBSTITUTED 2-AMINOALK-3-ENOIC ACIDS

Substituted 2-aminoalk-3-enoic acid derivative of formula I STR1 wherein R 1 is an aliphatic hydrocarbon radical that is substituted by optionally acylated or aliphatically or araliphatically etherified hydroxy, by halogen, by optionally acylated and/or aliphatically substituted amino or by an aza-, diaza-, azoxa-or oxa-cycloaliphatic radical, or is an oxacycloaliphatic hydrocarbon radical bonded via a carbon atom, or is an optionally aliphatically N-substituted or N-acylated azacycloaliphatic hydrocarbon radical, and R. sub.2 is free or esterified carboxy, and their salts exhibit NMDA-antagonistic properties and are useful as active ingredients of anticonvulsive medicaments.

Catalytic Asymmetric Synthesis of Alkyl Substituted Lactones by Enantioselective and Chemoselective Alkylation of Formylesters with Dialkylzincs Using N,N-Dibutylnorephedrine

Optically active 4-alkyl-γ-butyrolactones and 5-alkyl-6-valerolactones were obtained in high enantiomeric excesses (85-95percent e.e.) from the catalytic asymmetric alkylation of 3- and 4-formylesters with dialkylzincs using N,N-dibutylnorephedrine as catalyst.