14273-92-8

Usage

Uses

Used in Organic Synthesis:
5-Hydroxypentanoic acid methyl ester is used as a synthetic intermediate for the production of various organic compounds. Its chemical structure allows it to be a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-Hydroxypentanoic acid methyl ester is used as a key component in the development of new drugs. Its unique structure can be modified and functionalized to create novel drug candidates with potential therapeutic applications.
Used in Agrochemical Industry:
5-Hydroxypentanoic acid methyl ester is also utilized in the agrochemical industry for the synthesis of bioactive compounds, such as pesticides and herbicides. Its properties make it a valuable precursor for the development of new products with improved efficacy and reduced environmental impact.
Used in Specialty Chemicals:
5-Hydroxypentanoic acid methyl ester finds application in the production of specialty chemicals, such as fragrances, dyes, and additives. Its clear oil form and reactivity make it suitable for use in various chemical processes to create high-value products.

Synthesis Reference(s)

Canadian Journal of Chemistry, 52, p. 3651, 1974 DOI: 10.1139/v74-546Tetrahedron Letters, 30, p. 279, 1989 DOI: 10.1016/S0040-4039(00)95179-7

InChI:InChI=1/C6H12O3/c1-9-6(8)4-2-3-5-7/h7H,2-5H2,1H3

Upstream product

• 591235-26-6 ω-Diazo-n-valeriansaeure-methylester 
• 66607-28-1 2,2-dimethoxytetrahydropyran 
• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 118487-23-3 2-bromo-2-(4'-toluenesulphonyl)tetrahydropyran 
• 109-88-6 magnesium methanolate 
• 6026-86-4 methyl 4-formylbutanoate 
• 110-87-2 3,4-dihydro-2H-pyran 
• 124-04-9 Adipic acid 
• 1191-25-9 6-Hydroxyhexanoic acid 
• 556-48-9 1,4-Cyclohexanediol 
• 637-88-7 1,4-Cyclohexanedione 
• 1501-27-5 Pentanedioic acid, monomethyl ester 

Downstream Products

• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 6026-86-4 methyl 4-formylbutanoate 
• 1501-27-5 Pentanedioic acid, monomethyl ester 
• 81477-37-4 methyl 5-<(triphenylmethyl)oxy>pentanoate 
• 87729-38-2 5-(tert-butyldimethylsilanyloxy)pentanoic acid methyl ester 
• 111-29-5 1 ,5-pentanediol 
• 179690-97-2 5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid methyl ester 
• 216770-46-6 1-O-benzyl-5-O-[1-(4-methoxycarbonylbutyl)-2-(3-oxobutyl)]-phosphono-L-erythro-pent-2-ulose ethane-1,2-diyl dithioacetal 
• 489452-96-2 5-[N-(trichloroethoxycarbonyl)benzyloxyamino]pentanoic acid methyl ester 
• 1027079-22-6 5-(4-methoxy-phenoxy)-pentanoic acid methyl ester 
• 188697-89-4 4-[1-(triphenylmethyl)imidazol-4-yl]butan-1-ol 
• 887276-79-1 4-[4-(toluene-4-sulfonyl)-4,5-dihydrooxazol-5-yl]butyric acid methyl ester 
• 887276-93-9 dimethyl-[4-(1-trityl-1H-imidazol-4-yl)butyl]amine 
• 887276-85-9 isopropyl-[4-(1-trityl-1H-imidazol-4-yl)butyl]amine 

Relevant academic research and scientific papers

Total Synthesis of (+)-Guadinomic Acid via Hydroxyl-Directed Guanidylation

Protecting-group-free total synthesis of (+)-guadinomic acid is reported using δ-valerolactone as a readily available starting material. The protocol utilizes the recent hydroxyl-directed guanidylation of unactivated alkenes as an approach for direct stereoselective incorporation of the guanidine unit furnishing the natural product in 7 steps.

Molecular design of diene monomers containing an ester functional group for the synthesis of poly(diene sulfone)s by radical alternating copolymerization with sulfur dioxide

Functional poly(diene sulfone)s are prepared by the radical alternating copolymerization of 1,3-diene monomers containing an ester substituent with sulfur dioxide. Methyl 3,5-hexadienoate (MH) and methyl 5,7-octadienoate (MO) with both an alkylene spacer and a terminal diene structure are suitable to produce a high-molecular-weight copolymer in a high yield, while the copolymerization of 5,7-nonadienoic acid, ethyl 2,4-pentadienoate, and ethyl 4-methyl-2,4-pentadienoate including either an alkylene spacer or a terminal diene structure lead to unsuccessful results. The 13C NMR chemical shift values of MH and MO suggest a high electron density at their reacting α-carbon for exhibiting a high copolymerization reactivity. Fluorene-containing diene monomers, 9-fluorenyl 3,5-hexadienoate (FH) and 9-fluorenyl 5,7-octadienoate (FO), are also prepared and copolymerized with sulfur dioxide. The thermal and optical properties of the poly(diene sulfone)s containing the methyl and fluorenyl ester substituents in the side chain are investigated.

Structure-activity relationship study of flowering-inducer FN against Lemna paucicostata

FN1 (1) and FN2 (2), cycloadducts of α-ketol octadecadienoic acid (3) with norepinephrine (NE), induce flowering in Lemna paucicostata. In order to broaden our understanding of structural requirements of FN?for flower induction, nine analogs of 3 (4-12) were synthesized and reacted with NE under basic conditions. These analogs, except for 8, 10, and 12, exhibited significant activity regarding to floral induction in L. paucicostata. Similar experiments were carried out by using 3 and epinephrine, and it was demonstrated that these products also possessed biological activity.

Photocurable hard and porous biomaterials from ROMP precursors cross-linked with diyl radicals

A combination of (ROMP) ring-opening metathesis polymerization and diradical (diyl) cross-linking provides a new access to hard biomaterials and potential artificial bone replacements. ROMP was used to construct soft and pliable linear polymers bearing photolabile diazene functions. After treatment with light, a nitrogen aerosol is released throughout the polymer to create desirable porosity, cross-linking, and hardening in a single step. Nonpolymeric mechanistic work supporting these studies was also examined.

A convenient and mild procedure for the preparation of hydroxyesters from lactones and hydroxyacids

An alcoholic solution of lactones and hydroxyacids stored on Amberlyst-15 results in the formation of corresponding hydroxyesters in high yields.

Catalytic asymmetric synthesis of Leukotriene B4

Leukotriene B4 1 was prepared from two chiral synthons 8 and 14. The chiral secondary alcohols of 8 and 14 were constructed by BINOL/Ti(OiPr)4 catalyzed enantioselective alkynylzinc addition to aldehydes.

Mechanism-based inactivation of serine proteases by dichlorocyclopropane fused lactone derivatives

A dichlorocyclopropane fused lactone derivative was prepared as a novel mechanism-based inactivator of serine protease, α-chymotrypsin. The lactone derivative showed transient irreversible inhibitory activity toward α-chymotrypsin with the value of k(obsd)/[I] = 54 M-1s-1 and the enzyme activity recovered perfectly after 6 hours.

Oxidation of cyclic acetals by ozone in ionic liquid media

The application of ozone-stable pyrrolidinium based ionic liquids as safe reaction media resulted in selective hydroxy ester formation upon ozonation of cyclic acetals without using low temperatures or acetylating reagents.

Kinetic analysis of terminal and unactivated C-H bond oxyfunctionalization in fatty acid methyl esters by monooxygenase-based whole-cell biocatalysis

The alkane monooxygenase AlkBGT from Pseudomonas putida GPo1 constitutes a versatile enzyme system for the ω-oxyfunctionalization of medium chain-length alkanes. In this study, recombinant Escherichia coli W3110 expressing alkBGT was investigated as whole-cell catalyst for the regioselective biooxidation of fatty acid methyl esters to terminal alcohols. The ω-functionalized products are of general economic interest, serving as building blocks for polymer synthesis. The whole-cell catalysts proved to functionalize fatty acid methyl esters with a medium length alkyl chain specifically at the ω-position. The highest specific hydroxylation activity of 104 U gCDW-1 was obtained with nonanoic acid methyl ester as substrate using resting cells of E. coli W3110 (pBT10). In an optimized set-up, maximal 9-hydroxynonanoic acid methyl ester yields of 95% were achieved. For this specific substrate, apparent whole-cell kinetic parameters were determined with a Vmax of 204±9 U gCDW -1, a substrate uptake constant (KS) of 142±17 μM, and a specificity constant Vmax/KS of 1.4 U g CDW-1 μM-1 for the formation of the terminal alcohol. The same E. coli strain carrying additional alk genes showed a different substrate selectivity. A comparison of biocatalysis with whole cells and enriched enzyme preparations showed that both substrate availability and enzyme specificity control the efficiency of the whole-cell bioconversion of the longer and more hydrophobic substrate dodecanoic acid methyl ester. The efficient coupling of redox cofactor oxidation and product formation, as determined in vitro, combined with the high in vivo activities make E. coli W3110 (pBT10) a promising biocatalyst for the preparative synthesis of terminally functionalized fatty acid methyl esters. Copyright

Enantioselective Total Synthesis of (+)-Heilonine

Chemical transformations that rapidly and efficiently construct a high level of molecular complexity in a single step are perhaps the most valuable in total synthesis. Among such transformations is the transition metal catalyzed [2 + 2 + 2] cycloisomerization reaction, which forges three new C-C bonds and one or more rings in a single synthetic operation. We report here a strategy that leverages this transformation to open de novo access to the Veratrum family of alkaloids. The highly convergent approach described herein includes (i) the enantioselective synthesis of a diyne fragment containing the steroidal A/B rings, (ii) the asymmetric synthesis of a propargyl-substituted piperidinone (F ring) unit, (iii) the high-yielding union of the above fragments, and (iv) the intramolecular [2 + 2 + 2] cycloisomerization reaction of the resulting carbon framework to construct in a single step the remaining three rings (C/D/E) of the hexacyclic cevanine skeleton. Efficient late-stage maneuvers culminated in the first total synthesis of heilonine (1), achieved in 21 steps starting from ethyl vinyl ketone.