72345-34-7

Usage

Uses

Used in Organic Synthesis:
(2S,3S)-(+)-2-ALLYL-3-HYDROXY-2-METHYLCYCLOPENTANONE is utilized as a key intermediate in organic synthesis for the creation of more complex molecules. Its unique structure and functional groups make it a valuable building block for developing new compounds with a range of potential applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (2S,3S)-(+)-2-ALLYL-3-HYDROXY-2-METHYLCYCLOPENTANONE is employed as a precursor for the synthesis of pharmaceutically relevant molecules. Its chiral nature and specific functional groups contribute to the development of enantiomerically pure drugs with improved efficacy and reduced side effects.
Used in Antifungal Applications:
(2S,3S)-(+)-2-ALLYL-3-HYDROXY-2-METHYLCYCLOPENTANONE has demonstrated antifungal properties, making it a potential candidate for use in antifungal agents. It can be utilized in the development of new treatments for fungal infections, offering an alternative to existing antifungal drugs.
Used in Antimicrobial Applications:
The antimicrobial activity of (2S,3S)-(+)-2-ALLYL-3-HYDROXY-2-METHYLCYCLOPENTANONE also positions it as a candidate for use in antimicrobial agents. It can contribute to the development of new antibiotics or disinfectants to combat bacterial infections, particularly in the context of increasing antibiotic resistance.
Used in Pharmaceutical Industry:
(2S,3S)-(+)-2-ALLYL-3-HYDROXY-2-METHYLCYCLOPENTANONE is used in the pharmaceutical industry as a starting material for the synthesis of drug candidates. Its unique structural features and biological activities make it a promising compound for the development of novel therapeutic agents with potential applications in various medical conditions.
Used in Industrial Applications:
Beyond its uses in medicine, (2S,3S)-(+)-2-ALLYL-3-HYDROXY-2-METHYLCYCLOPENTANONE can also find applications in various industrial sectors. Its chemical properties and reactivity make it suitable for use in the synthesis of specialty chemicals, materials, and other products that require specific functional groups and chiral centers.

InChI:InChI=1/C9H14O2/c1-3-6-9(2)7(10)4-5-8(9)11/h3,7,10H,1,4-6H2,2H3/t7-,9-/m0/s1

Upstream product

• 26828-48-8 2-allyl-2-methyl-1,3-cyclopentanedione 
• 765-69-5 2-Methylcyclopentane-1,3-dione 

Downstream Products

• 84736-06-1 Toluene-4-sulfonic acid (1S,2S)-2-allyl-2-methyl-3-oxo-cyclopentyl ester 
• 871823-46-0 [(Z)-(R)-8-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enyl)-4-methoxymethoxy-2,6-dimethyl-oct-6-enyloxy]-tert-butyl-dimethyl-silane 
• 871823-42-6 (Z)-6-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enyl)-2-hydroxy-2-((R)-3-hydroxy-2-methyl-propyl)-4-methyl-hex-4-enenitrile 
• 871823-35-7 (Z)-4-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enyl)-2-methyl-but-2-en-1-ol 
• 871823-29-9 4-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enylmethyl)-2,2-dimethyl-[1,3]dioxolane 
• 871823-31-3 ((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enyl)-acetaldehyde 
• 871823-44-8 (Z)-(R)-8-((S)-2-Benzyloxymethyl-1-methyl-cyclopent-2-enyl)-1-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-oct-6-en-4-one 
• 871823-53-9 [(S)-5-((Z)-4-Chloro-3-methyl-but-2-enyl)-5-methyl-cyclopent-1-enylmethoxymethyl]-benzene 
• 932024-64-1 C₃₀H₄₅IO₂Si₂ 
• 932024-72-1 C₄₁H₅₄O₅Si 
• 932024-76-5 C₃₄H₄₈O₃Si₂ 

Relevant academic research and scientific papers

Highly stereocontrolled reduction of 1,3-cyclopentanediones using oxazaborolidine -BH3

Highly enantioselective reduction of 1,3-cyclopentanediones was conducted using an oxazaborolidine derived from L-threonine and a borane complex to give either 1,3-cyclopentanediols or 3-hydroxycyclopentanones in high enantiomeric purity by choosing appropriate reduction conditions. Copyright (C) 2000 Elsevier Science Ltd.

Desymmetric enantioselective reduction of cyclic 1,3-diketones catalyzed by a recyclable p-chiral phosphinamide organocatalyst

The P-stereogenic phosphinamides are a structurally novel skeletal class which has not been investigated as chiral organocatalysts. However, chiral cyclic 3-hydroxy ketones are widely used as building blocks in the synthesis of natural products and bioactive compounds. However, general and practical methods for the synthesis of such chiral compounds remain underdeveloped. Herein, we demonstrate that the P-stereogenic phosphinamides are powerful organocatalysts for the desymmetric enantioselective reduction of cyclic 1,3-diketones, providing a useful method for the synthesis of chiral cyclic 3-hydroxy ketones. The protocol displays a broad substrate scope that is amenable to a series of cyclic 2,2-disubstituted five- and six-membered 1,3-diketones. The chiral cyclic 3-hydroxy ketone products bearing an all-carbon chiral quaternary center could be obtained with high enantioselectivities (up to 98% ee) and diastereoselectivities (up to 99:1 dr). Most importantly, the reactions could be practically performed on the gram scale and the catalysts could be reused without compromising the catalytic efficiency. Mechanistic studies revealed that an intermediate formed from P-stereogenic phosphinamide and catecholborane is the real catalytically active species. The results disclosed herein bode well for designing and developing other reactions using P-stereogenic phosphinamides as new organocatalysts.

Stereoselective Reduction of Prochiral Cyclic 1,3-Diketones Using Different Biocatalysts

We have developed biocatalytic methods for the stereoselective reduction of cyclic prochiral 1,3-diketones for the production of optically active β-hydroxyketones and/or 1,3-diols. The recombinant ketoreductase KRED1-Pglu (formulated as purified catalyst)

Structure-Guided Directed Evolution of a Carbonyl Reductase Enables the Stereoselective Synthesis of (2 S,3 S)-2,2-Disubstituted-3-hydroxycyclopentanones via Desymmetric Reduction

In this study, an engineered carbonyl reductase (M4) was obtained through structure-guided directed evolution of a carbonyl reductase (SSCR) from Sporobolomyces salmonicolor AKU4429. Mutant M4 showed 23.9-fold enhancement of enzyme activity toward the model substrate 2-methyl-2-benzyl-1,3-cyclopentanedione, affording the (2S,3S)-stereoisomer in >98percent ratio. This variant also showed excellent stereoselectivity toward most of the tested substrates, offering a valuable biocatalyst for the stereoselective reduction of these cyclic diketones to access the corresponding (2S,3S)-2,2-disubstituted-3-hydroxyketones.

Synthetic Studies on Enantioselective Total Synthesis of Cyathane Diterpenoids: Cyrneines A and B, Glaucopine C, and (+)-Allocyathin B2

The details for the synthetic studies on enantioselective total synthesis of cyathane diterpenoids cyrneine A (1) and B (2), glaucopine C (3), and (+)-allocyathin B2 are presented. We established a mild Suzuki coupling for heavily substituted n

A Total Synthesis of (-)-Hamigeran B and (-)-4-Bromohamigeran B

A concise synthesis of (-)-hamigeran B and (-)-4-bromohamigeran B is presented. The key reactions include a Suzuki coupling of enol triflate 15 with arylboronic ester for efficient synthesis of the densely 1,2,3-trisubstituted cyclopentene 23, a coordinat

Efforts toward rapid construction of the cortistatin A carbocyclic core via enyne-ene metathesis

Our efforts toward the construction of the carbocylic core of cortistatin A via an enyne-ene metathesis are disclosed. Interestingly, an attempted S N2 inversion of a secondary mesylate in our five-membered D-ring piece gave a product with rete

Preparation of all stereoisomers of 2-allyl-2-methyl-3-hydroxycyclopentanone by desymmetric processes based on a microbial oxidation and reduction system

All stereoisomers of 2-allyl-3-hydroxy-2-methylcyclopentanones 2-5 were prepared in high conversion and in an optically pure form by microbial reduction and oxidation. The reduction of symmetric diketone 1 by Geotrichum candidum NBRC 4597 under anaerobic conditions gave 2 in 83% yield (98% conversion), >99% de, and >99% ee, whereas the reduction of 1 by G. candidum NBRC 5767 under aerobic conditions gave 3 in 75% yield (99% conversion), >99% de, and >99% ee. Oxidation of meso-diol 6 by G. candidum NBRC 5767 under aerobic conditions afforded 4 in 83% yield (99% conversion) and >99% ee, while oxidation of meso-diol 7 by Mucor heimalis IAM 6095 in the presence of cyclohexanone as a co-oxidant afforded 5 in 68% yield (75% conversion) and >99% ee.

Comparative reductive desymmetrization of 2,2-disubstituted-cycloalkane-1,3-diones

Reductive desymmetrization of 2-methyl-2-substituted-cycloalkane-1,3-diones can be effected using either NaBH4 in DME or lithium tri-tert-butoxyaluminum hydride (LTBA) in THF at -60 °C. The former is a new approach that offers slightly greater

Enantioselective total synthesis of (+)-digitoxigenin

An enantioselective total synthesis of (+)-digitoxigenin is described. This total synthesis is accomplished in a convergent manner using two chiral fragments prepared via the catalytic asymmetric intramolecular cyclopropanation and baker's yeast mediated reduction developed by us, respectively. This convergent synthesis would be useful for preparing some new derivatives of digitoxigenin for SAR studies and could be applied for the total synthesis of other cardenolides left unprepared.