303156-68-5

Usage

Molecular structure

2,4-Octadienoic acid, 8-hydroxy-6-(hydroxymethyl)-4-methyl-, (2R,3R)-3,6-dihydro-6-oxo-2-[(1S,3R,5E)-1,3,5-trimethyl-5-heptenyl]-2H-pyran-3-yl ester, (2E,4E,6S)is a complex organic compound with a carboxylic acid group, a hydroxymethyl group, a methyl group, and a pyran ring.

Stereochemistry

The compound has multiple stereocenters, specifically two R configurations at carbons 2 and 3, and an S configuration at carbon 6.

Double bonds

The compound contains two double bonds, indicated by the "2,4-Octadienoic acid" and "(1S,3R,5E)-1,3,5-trimethyl-5-heptenyl" parts of its name.

Biological activity

The compound has potential biological activity, which may be utilized in pharmaceutical or agrochemical applications.

Molecular weight

The molecular weight of the compound is 360.42 g/mol.

Physical state

At room temperature, the compound is likely a solid, as most organic compounds with similar molecular weights and complexities are.

Solubility

The compound may be soluble in organic solvents such as ethanol, methanol, or acetone, but its exact solubility profile would depend on its polarity and molecular interactions.

Upstream product

• 911708-89-9 (5R)-5-[(1R,2S,4R,6E)-(2,4,6-trimethyl-1-trimethylsilanyloxy-6-octenyl)]-2,5-dihydrofuran-2-ol 
• 911708-91-3 (5R,6R)-6-((2S,4R,E)-4,6-dimethyloct-6-en-2-yl)-5-((trimethylsilyl)oxy)-5,6-dihydro-2H-pyran-2-one 
• 1417795-86-8 C₂₃H₃₂O₃Si 
• 1417795-87-9 ((2S,4R)-4-((4-methoxybenzyloxy)methyl)-2-methylpentyloxy)(tert-butyl)diphenylsilane 
• 157837-64-4 (2R,4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-2,4-dimethylpentan-1-ol 
• 143236-77-5 [2S,4R]-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentan-1-ol 
• 143236-78-6 (2S,4R)-5-(4-methoxybenzyloxy)-2,4-dimethylpentanal 
• 1417795-90-4 (2S,4R)-5-(4-methoxybenzyloxy)-1-(furan-2-yl)-2,4-dimethylpentan-1-ol 
• 1417795-91-5 (2S,4R)-5-(4-methoxybenzyloxy)-1-(furan-2-yl)-2,4-dimethylpentan-1-one 
• 911708-88-8 (R)-5-((1R,2S,4R,E)-2,4,6-trimethyl-1-((trimethylsilyl)oxy)oct-6-en-1-yl)furan-2(5H)-one 
• 637000-46-5 ethyl (S,E)-6-((tert-butyldimethylsilyl)oxy)-4-(((tert-butyldimethylsilyl)oxy)methyl)2-methylhex-2-enoate 
• 848737-79-1 (-)-(5R,6R)-6-((2S,4R,E)-4,6-dimethyloct-6-en-2-yl)-5-hydroxy-5,6-dihydro-2H-pyran-2-one 
• 848738-03-4 (2E, 4E, 6S)-8-(tert-butyldimethylsilanyloxy)-6-(tert-butyldimethylsilanyloxymethyl)-4-methyl-2,4-octadienoic acid 
• 1417796-04-3 (S,2E,4E)-8-(tert-butyldiphenylsilyloxy)-6-((tert-butyldiphenylsilyloxy)methyl)-4-methylocta-2,4-dienoic acid 

Relevant academic research and scientific papers

Scalable Synthesis of (-)-Rasfonin Enabled by a Convergent Enantioselective α-Hydroxymethylation Strategy

A scalable synthesis of the potent antitumor agent, (-)-rasfonin, has been achieved. The synthetic strategy features a highly convergent approach based on a single protocol construction of both major fragments via catalytic enantioselective α-hydroxymethylation of simple aliphatic aldehydes. The route described has been successful in the generation of gram quantities of the natural product and serves as the first synthetic strategy to provide sufficient material to continue studies related to its mechanism of action and potential as a cancer therapeutic.

Asymmetric total synthesis of (-)-rasfonin

An efficient chemoenzymatic asymmetric synthesis of pyranone containing natural product (-)-rasfonin is presented here. Enantioselective enzymatic desymmetrization (EED) and a unique Gluconobacter oxydans mediated oxidative kinetic resolution (OKR) have been successfully employed to install three stereocenters (C6′, C7, and C9) of the target molecule. Stereoselective Achmatowicz reaction of a properly decorated furyl nucleus led to the core pyranone structure of rasfonin. At the late stage of the synthesis Negishi coupling has been used to complete the synthesis.

A concise asymmetric synthesis of (-)-rasfonin

A very efficient total synthesis of the apoptosis inducer (-)-rasfonin has been developed using CuBr/JosiPhos catalyzed iterative asymmetric conjugate addition of MeMgBr and Feringa's butenolide.

Toward the development of a general chiral auxiliary. Enantioselective alkylation and a new catalytic asymmetric addition of silyloxyfurans: Application to a total synthesis of (-)-rasfonin

An enantioselective total synthesis of the apoptosis-inducing natural product, (-)-rasfonin, is described. Camphor lactam-mediated asymmetric alkylation reactions enabled the installation of three stereogenic centers with >95:5 diastereoselectivity. A modified Corey-Peterson olefination was employed in the construction of the (E,E)-diene system. A highly diastereoselective, asymmetric vinylogous Mukaiyama aldol addition was conducted using a chiral cationic oxazaborolidine catalyst. The pyranone core of the natural product was prepared via a DBU-promoted rearrangement of a furanol to its corresponding pyranol with concomitant [1,4]-silyl transfer. Copyright

Total synthesis of TT-1 (rasfonin), an α-pyrone-containing natural product from a fungus Trichurus terrophilus

Total synthesis of TT-1 (1=rasfonin), an α-pyrone-containing natural product from a Fungi Imperfecti Trichurus terrophilus culture was achieved by a stereoselective method in optically active form, which further provided evidence for the whole structure of TT-1 (1) including the absolute stereochemistry.