587885-30-1

Upstream product

• 51410-44-7 1-(4-methoxylphenyl)-2-propen-1-ol 
• 2768-02-7 (vinyl)trimethoxylsilane 
• 123-11-5 4-methoxy-benzaldehyde 
• 65313-35-1 trivinylbismuthine 
• 108-05-4 vinyl acetate 
• 7448-86-4 1-(4-methoxyphenyl)prop-2-en-1-one 
• 97-72-3 2-Methylpropionic anhydride 
• 123-62-6 propionic acid anhydride 
• 94607-41-7 (E)-1-(4-methoxyphenyl)-3-chloropropene 

Downstream Products

• 587885-32-3 (S,S)-acetic acid 2,4-bis(4-methoxyphenyl)-4-oxo-1-triethylsilanyloxymethyl-butyl ester 
• 587885-31-2 (R)-1,3-bis-(4-methoxyphenyl)pent-4-en-1-one 
• 136031-29-3 (-)-sugiresinol dimethyl ether 

Relevant academic research and scientific papers

Structural Modification of Natural Product Ganomycin i Leading to Discovery of a α-Glucosidase and HMG-CoA Reductase Dual Inhibitor Improving Obesity and Metabolic Dysfunction in Vivo

It is a great challenge to develop drugs for treatment of metabolic syndrome. With ganomycin I as a leading compound, 14 meroterpene derivatives were synthesized and screened for their α-glucosidase and HMG-CoA reductase inhibitory activities. As a result, a α-glucosidase and HMG-CoA reductase dual inhibitor ((R,E)-5-(4-(tert-butyl)phenyl)-3-(4,8-dimethylnona-3,7-dien-1-yl)furan-2(5H)-one, 7d) with improved chemical stability and long-term safety was obtained. Compound 7d showed multiple and strong in vivo efficacies in reducing weight gain, lowering HbAlc level, and improving insulin resistance and lipid dysfunction in both ob/ob and diet-induced obesity (DIO) mice models. Compound 7d was also found to reduce hepatic steatosis in ob/ob model. 16S rRNA gene sequencing, SCFA, and intestinal mucosal barrier function analysis indicated that gut microbiota plays a central and causative role in mediating the multiple efficacies of 7d. Our results demonstrate that 7d is a promising drug candidate for metabolic syndrome.

Isothiourea-Catalysed Acylative Kinetic Resolution of Aryl–Alkenyl (sp2vs. sp2) Substituted Secondary Alcohols

The non-enzymatic acylative kinetic resolution of challenging aryl–alkenyl (sp2vs. sp2) substituted secondary alcohols is described, with effective enantiodiscrimination achieved using the isothiourea organocatalyst HyperBTM (1 mol %) and isobutyric anhydride. The kinetic resolution of a wide range of aryl–alkenyl substituted alcohols has been evaluated, with either electron-rich or naphthyl aryl substituents in combination with an unsubstituted vinyl substituent providing the highest selectivity (S=2–1980). The use of this protocol for the gram-scale (2.5 g) kinetic resolution of a model aryl–vinyl (sp2vs. sp2) substituted secondary alcohol is demonstrated, giving access to >1 g of each of the product enantiomers both in 99:1 e.r.

Kinetic resolution of allylic alcohols via stereoselective acylation catalyzed by lipase PS-30

By using lipase PS-30 as catalyst, the kinetic resolution of a series of racemic allylic alcohols has been achieved via stereoselective acylation. The value of kinetic enantiomeric ratio (E) reached up to 968. Substituent effect is briefly discussed.

Ruthenium-catalyzed regio- and enantioselective allylic substitution with water: Direct synthesis of chiral allylic alcohols

Less is more: A new route to access chiral allylic alcohols through the regio- and enantioselective substitution of monosubstituted allylic chlorides with water has been developed. The reaction is catalyzed effectively by planar-chiral cyclopentadienyl ruthenium complexes (see scheme). Copyright

Highly diastereo- and enantio-selective epoxidation of secondary allylic alcohols catalyzed by styrene monooxygenase

Enantiomerically enriched glycidol derivatives with contiguous stereogenic centers were obtained in a highly diastereo- and enantio-selective epoxidation catalyzed with the styrene monooxygenase StyAB2.

Chiral phosphonite, phosphite and phosphoramidite η6-arene- ruthenium(ii) complexes: Application to the kinetic resolution of allylic alcohols

The synthesis and characterization of chiral arene-ruthenium complexes [RuCl2(η6-arene){(R)-PR(binaphthoxy)}] (arene = benzene (1), p-cymene (2), mesitylene (3); R = Ph (a), OPh (b), piperidyl (c)) are described. Derivatives 1-3 have been employed to promote the kinetic resolution of allylic alcohols through a redox-isomerization process. As a general trend, the best selectivities are attained with the more sterically hindered catalysts i.e. those containing p-cymene or mesitylene ligands. The Royal Society of Chemistry 2010.

A highly enantioselective synthesis of chiral allylic alcohols by asymmetric addition of novel mixed reagents of trialkenylbismuthines/dialkylzincs to aldehydes

A novel mixture of reagents of trialkenylbismuthines/dialkylzincs was developed and applied toward the synthesis of chiral allylic alcohols. The chiral β-amino alcohols catalyzed addition of the mixed reagents of trialkenylbismuthines/dialkylzincs to alde

Enantioselective alkenylation and phenylation catalyzed by a chiral CuF complex

A new method for CuF-catalyzed alkenylation and phenylation of aldehydes and an activated ketone using air- and moisture-stable alkenylsilanes and phenylsilane as a nucleophile is described. This methodology was extended to highly enantioselective catalytic alkenylation and phenylation using DTBM-SEGPHOS as a chiral ligand. Substrate generality is broad, and an alkenylsilane with a long alkyl chain and an internal alkenylsilane can be also used as a nucleophile. The key to success partly involves the accelerated regeneration of reactive alkenylcopper and phenylcopper through transmetalation from the silylated nucleophiles, and stabilization of the reactive copper reagents, both of which are effected by the diphosphine ligands. Copyright

Regioselective and enantiospecific rhodium-catalyzed allylic alkylation reactions using copper(I) enolates: Synthesis of (-)-sugiresinol dimethyl ether

The transition metal-catalyzed allylic alkylation represents a fundamentally important cross-coupling reaction for the construction of ternary carbon stereogenic centers. We have developed a regioselective and enantiospecific rhodium-catalyzed allylic alk