114264-05-0

Usage

Uses

Used in Organic Synthesis:
(3S,4S)-4-((R)-2(benzyloxy)tridecyl)-3-hexyl-2-oxetanone is used as an intermediate in organic synthesis for the creation of complex molecules and pharmaceutical compounds. Its unique structure allows for various chemical reactions and modifications, making it a versatile building block in the synthesis of novel organic compounds.
Used in Pharmaceutical Industry:
(3S,4S)-4-((R)-2(benzyloxy)tridecyl)-3-hexyl-2-oxetanone is used as a chiral scaffold in drug design for the development of new pharmaceuticals. Its chiral nature provides opportunities for asymmetric synthesis, which can lead to the creation of enantiomerically pure drugs with improved efficacy and reduced side effects.
Used in Materials Science:
(3S,4S)-4-((R)-2(benzyloxy)tridecyl)-3-hexyl-2-oxetanone is used as a component in the development of advanced materials with specific properties. The presence of the benzyloxy group can be exploited for selective functionalization of aromatic compounds, which can be beneficial in the synthesis of materials with tailored characteristics for various applications.
Used in Chemical Reactions:
(3S,4S)-4-((R)-2(benzyloxy)tridecyl)-3-hexyl-2-oxetanone is used as a reactant in chemical reactions that involve selective functionalization of aromatic compounds. The benzyloxy group can be selectively modified, allowing for the synthesis of a range of derivatives with potential applications in various industries, including pharmaceuticals and materials science.

Upstream product

• 125564-93-4 3-hexyl-3-trimethylsilyl-4-<(R)-2'-(benzyloxy)tridecyl>-2-oxetanone 
• 114299-20-6 (2S,3S,5R)-5-(benzyloxy)-3-hydroxy-2-hexylhexadecanoic acid 
• 112-54-9 Dodecanal 
• 100-39-0 benzyl bromide 
• 28715-21-1 (R)-3-hydroxytetradecanoic acid 
• 14273-09-7 1-ethoxy-1-octyne 
• 98-09-9 benzenesulfonyl chloride 
• 638-45-9 1-Iodohexane 
• 139623-16-8 (R)-3-benzyloxy-1-hydroxytetradecane 
• 112763-97-0 (R)-3-phenylmethyloxy-tetradecanal 
• 220583-64-2 Benzoic acid (1R,3S,4S,6R)-6-benzyloxy-3-hexyl-4-hydroxy-1-methyl-2-oxo-heptadecyl ester 
• 220583-66-4 (2R,4S,5S,7R)-7-Benzyloxy-4-hexyl-octadecane-2,3,5-triol 
• 220583-65-3 (R)-2-(benzoyloxy)decan-2-one 
• 383416-55-5 (R)-2-Hydroxy-decan-3-one 

Downstream Products

• 68711-40-0 (3S,4S)-3-hexyl-4-[(R)-2-hydroxytridecyl]-2-oxetanone 
• 104872-04-0 Orlistat 

Relevant academic research and scientific papers

METHOD FOR PREPARING (3S,4S)-4-((R)-2-(BENZYLOXY)TRIDECYL)-3-HEXYL-2-OXETANONE AND NOVEL INTERMEDIATE USED THEREFOR

The present invention relates to a high-yield method for preparing highly pure (3S,4S)-4-((R)-2-(benzyloxy)tridecyl)-3-hexyl-2-oxetanone using a metal salt of (2S,3S,5R)-2-hexyl-3,5-dihydroxyhexadecanoic acid as an intermediate.

Stereoselective syntheses of (-)-tetrahydrolipstatin via Prins cyclisations

Stereoselective syntheses of (-)-tetrahydrolipstatin have been achieved via two divergent approaches through Prins cyclisations as the key steps. PCC mediated oxidative cleavage, Frater alkylation, Keck allylation, Sharpless asymmetric epoxidation and allylic cleavage were the other key steps employed.

Stereoselective synthesis of (-)-tetrahydrolipstatin via a radical cyclization based strategy

An efficient and flexible approach for the total synthesis of (-)-tetrahydrolipstatin is described. The main features of the synthetic strategy are a stereocontrolled radical cyclization and the successful utilization of commercially available S-malic acid.

Anti-aldol reactions of lactate-derived ketones. Application to the synthesis of (-)-tetrahydrolipstatin

(-)-Tetrahydrolipstatin (1) was prepared with a high level of stereocontrol (>98% ds) by employing a boron-mediated, anti-selective, aldol coupling between the (R)-lactate-derived ketone 7 and the aldehyde 8.

An asymmetric synthesis of (-)-tetrahydrolipstatin

A key step in a short asymmetric synthesis of the potent pancreatic lipase inhibitor (-)-tetrahydrolipstatin (2) is a Lewis acid-catalysed [2 + 2] cycloaddition of n-hexyl(trimethylsilyl)ketene (5) to (R)-3-(tertbutyldimethylsilyloxy)tetradecanal (4a).

Total synthesis of (-)-tetrahydrolipstatin

The total synthesis of (-)-tetrahydrolipstatin utilizing two approaches is described. In the first, L-malic acid was used as a chiral template to obtain enantiomerically pure (R)-3-(benzyloxy)-tetradecanal (11) which was chain- extended using 1-(trimethylsilyl)-2-nonene and a Lewis acid. This advanced intermediate was further elaborated to the target compound in good overall yield. The second approach utilized lauraldehyde as a starting material and capitalizes on an asymmetric allylboronation (91% ee). The product could be obtained enantiomerically pure by conversion to the (R)-acetoxymandelate ester and hydrolysis. Oxidative cleavage of the terminal double bond led to 11 which was further extended using 1,3- and 1,2-asymmetric induction based on existing neighboring chirality. The synthesis of tetrahydrolipstatin using the second approach comprises seven steps from 11 and proceeds in 38% overall yield.