160666-92-2

Usage

Uses

Used in Pharmaceutical Industry:
3-Pentanone, 2-(benzoyloxy)-, (2S)is used as a reagent in the pharmaceutical industry for the synthesis of chiral compounds. The (S)-enantiomer of 3-Pentanone, 2-(benzoyloxy)-, (2S)- is particularly valuable due to its specific stereochemistry, which is crucial for the development of enantiomerically pure drugs that can have different biological activities and effects.
Used in Organic Synthesis:
In the field of organic synthesis, 3-Pentanone, 2-(benzoyloxy)-, (2S)serves as a key intermediate for the preparation of various complex organic molecules. Its unique structure and reactivity make it a versatile building block for creating a wide range of chemical products, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research and Development:
3-Pentanone, 2-(benzoyloxy)-, (2S)is also utilized in research and development settings to explore new synthetic routes, develop innovative methodologies, and improve existing processes. Its application in this context helps advance the understanding of stereoselective reactions and contributes to the discovery of new chiral molecules with potential applications in various industries.

Upstream product

• 125948-63-2 (S)-2-hydroxypentan-⁽³⁾-one 
• 93-97-0 benzoic acid anhydride 
• 132489-33-9 (S)-2-benzyloxy-3-pentanone 
• 98-88-4 benzoyl chloride 
• 925-90-6 ethylmagnesium bromide 
• 177905-46-3 (S)-2-hydroxy-N-methoxy-N-methyl-propionamide 
• 27871-49-4 (S)-Methyl lactate 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 

Downstream Products

• 160666-93-3 Benzoic acid (E)-(1S,3R,4S)-4-hydroxy-1,3,5-trimethyl-2-oxo-hept-5-enyl ester 
• 164145-54-4 (2S,4R,5R,6S)-2-Benzoyloxy-7-benzyloxy-5-hydroxy-4,6-dimethylheptan-3-one 
• 164145-57-7 (1S,2R,4S)-4-Benzoyloxy-1-hydroxy-2-methyl-1-phenylpentan-3-one 
• 164145-56-6 (2S,4R,5R)-2-benzoyloxy-5-hydroxy-4-methylpentan-3-one 
• 173726-06-2 (2S,4R,5R,6E)-2-benzoyloxy-5-hydroxy-4-methyloct-6-en-3-one 
• 207680-79-3 (2S,4R,5R,6R)-7-(benzyloxy)-5-hydroxy-4,6-dimethyl-3-oxoheptan-2-yl benzoate 
• 306275-06-9 Benzoic acid (E)-(1S,3R,4S,7S,9R)-4-hydroxy-1,3,5,7,9-pentamethyl-2-oxo-undec-5-enyl ester 
• 332179-83-6 Benzoic acid (1S,3R,4R)-6-benzyloxy-4-hydroxy-1,3-dimethyl-2-oxo-hexyl ester 
• 797758-67-9 (2S,4R,5S,6E,8R)-2-benzoyloxy-4,6,8-trimethyl-5-hydroxyundec-6-en-3-one 
• 875289-37-5 (2S,4R,5R,6S)-2-benzyloxy-5-hydroxy-4,6-dimethyloctan-3-one 
• 888488-42-4 (2S,4R,5R,6S,7R)-2-benzoyloxy-7-tert-butyldimethylsilyloxy-5-hydroxy-4,6,8-trimethylnon-3-one 
• 942133-08-6 (2S,4R,5R,E)-5-hydroxy-9-(4-methoxybenzyloxy)-4,7-dimethyl-3-oxonon-6-en-2-yl benzoate 

Relevant academic research and scientific papers

A Highly Convergent and Biomimetic Total Synthesis of Portentol

An efficient total synthesis of the unusual polyketide portentol is reported. Three boron aldol reactions were used to assemble the linear carbon chain of the natural product, which contains two challenging anti-anti stereotriads. A biomimetic double cyclization cascade, triggered by an oxidation, then afforded portentol and its known dehydration product, anhydroportentol. The biosynthesis of portentol and the biosynthetic relevance of our key step are discussed.

Total Synthesis of Archazolid F

A partial bioinspired as well as the total synthesis of archazolid F, a highly potent V-ATPase inhibitory, antiproliferative polyketide macrolide, is described. Key features of the synthetic routes include a highly stereoselective aldol condensation of tw

Design, Synthesis and Biological Evaluation of Highly Potent Simplified Archazolids

The archazolids are potent antiproliferative compounds that have recently emerged as a novel class of promising anticancer agents. Their complex macrolide structures and scarce natural supply make the development of more readily available analogues highly important. Herein, we report the design, synthesis and biological evaluation of four simplified and partially saturated archazolid derivatives. We also reveal important structure-activity relationship data as well as insights into the pharmacophore of these complex polyketides.

Nhatrangin A: Total Syntheses of the Proposed Structure and Six of Its Diastereoisomers

A total synthesis of the proposed structure of nhatrangin A is described. This strategy relies on two aldol reactions to install the chiral centers at C3/C4 and C3′/C4′, a lithium-mediated coupling between an advanced intermediate alkyne and a Weinreb amide to complete the C1-C13 alkyl scaffold, and a Yamaguchi esterification to set the side chain. Discrepancies in the spectroscopic data between synthetic and natural nhatrangins led us to synthesize six more diastereoisomers of the proposed structure of nhatrangin A.

Stereocontrolled total synthesis of (+)-concanamycin F: The strategic use of boron-mediated aldol reactions of chiral ketones

A highly stereocontrolled total synthesis of the 18-membered macrolide (+)-concanamycin F, a potent inhibitor of vacuolar ATPases, is described that proceeds in 5.8% yield over 26 steps. The three key fragments, C1-C13 vinyl iodide, C14-C22 vinyl stannane

Synthesis of C13-C23 fragment of Iriomoteolide-1a

Highly efficient asymmetric conjugate addition of MeMgBr to α,β-unsaturated esters catalyzed by CuI/To1-BINAP, Paterson aldol, organocatalytic aldol, and cross-metathesis reactions were applied in the synthesis of C13-C23 fragment of Iriomoteolide-la.

Diastereodivergent Aldol reactions of β-alkoxy ethyl ketones: Modular access to (1,4)-syn and -anti polypropionates

(Chemical Equation Presented) Asymmetric substrate-controlled aldol reactions of ethyl ketones of type 4 with aldehyde 3 are reported. Modular access to all possible syn-and anti-aldol products was obtained by careful choice of reaction conditions. To ach

Polyketide synthesis using the boron-mediated, anti-aldol reactions of lactate-derived ketones: Total synthesis of (-)-ACRL toxin IIIB

The boron-mediated, anti-selective, aldol reactions of ketone 2 (and related derivatives) proceed with high levels of asymmetric induction, diastereoselectivities of up to 200:1 in favour of the aldol adducts 4 are obtained with achiral aldehydes and reag

Biosynthesis of tetronasin: Part 7. Preparation of structural analogues of the tetraketide biosynthetic precursor to tetronasin

The preparation of three structural analogues of the putative tetraketide biosynthetic precursor (2) of the acyl tetronic acid ionophore tetronasin, as N-acetylcysteamine thioesters (3), (4) and (5) is described. Two examples are 19F-labelled.

Studies in polypropionate synthesis: High π-face selectivity in Syn and Anti aldol reactions of chiral boron enolates of lactate-derived ketones

Use of (c)Hex2Bcl/Me2NEt in the aldol reactions of the α'-benzoyloxy ketone 7 with aldehydes leads to high stereoselectivity (97-95.5% ds) for the crystalline anti adducts 11. Under similar conditions, the corresponding benzyl ether 6 favours formation of the syn adducts 9.