119619-41-9

Upstream product

• 98-01-1 furfural 
• 623-48-3 ethyl iodoacetae 
• 105-36-2 ethyl bromoacetate 
• 4421-54-9 hydroxyvinyl ethyl ether 
• 4071-88-9 trimethylsilanyl-acetic acid ethyl ester 
• 56579-97-6 lithium 1-ethoxyethenolate 
• 141-78-6 ethyl acetate 

Downstream Products

• 14032-66-7 5-hydroxy-2-(5H)-furanone 
• 1192712-72-3 2-((2S,4S,6S)-4-(4-methoxybenzyloxy)-6-phenyl-tetrahydro-2H-pyran-2-yl)-1-phenylethanone 

Relevant academic research and scientific papers

Using water, light, air and spirulina to access a wide variety of polyoxygenated compounds

A new set of completely green methods utilising air, light, water and spirulina to transform readily accessible furan substrates into a diverse range of synthetically useful polyoxygenated motifs commonly found in natural products is presented herein. The Royal Society of Chemistry 2012.

Synthesis and biological evaluation of 12-, 13-, 14-membered macrolides and open chain 2,6-trans-disubstituted dihydropyran analogues for aspergillides

Stereoselective synthesis of twenty (three 12-, five 13- and twelve 14-membered) macrolides and seventeen functionalized 2,6-trans-disubstituted dihydropyran derivatives have been achieved. The key reactions include an Achmatowicz rearrangement, Ferrier-type alkynylation, Yamaguchi macrolactonization and Lindlar's hydrogenation. Biological screening of the synthesised compounds showed moderate activity against human cancer cell-lines.

Lipases A and B from Candida antarctica in the enantioselective acylation of ethyl 3-heteroaryl-3-hydroxypropanoates: Aspects on the preparation and enantiopreference

The preparative scale kinetic resolution of racemic ethyl 2- and 3-furyl- and 2- and 3-thienyl-3-hydroxypropanoates has been performed by Candida antarctica lipases A and B with vinyl esters. A study based on the present work together with the literature has been carried out in terms of lipase enantiopreference and substrate structure. We also discuss the excellent behavior of the lipase A in O-acylations of secondary alcohols with respect to enantiopreference.

Synthesis method of beta-hydroxy ester compound

The invention belongs to the technical field of medicine and organic chemical synthesis, and discloses a synthesis method of a beta-hydroxy ester compound. An aldehyde compound and an iodo-acetate compound are used as raw materials; manganese powder is adopted as an accelerant, metal nickel salt is adopted as a catalyst and an organic solvent is adopted as a reaction medium, an organic protonic acid is added and stirred and reacted under inert gas protection, the reaction system is cooled to room temperature after the reaction is finished, vacuum distillation and concentration are performed toobtain a crude product, and column chromatography purification is performed to obtain the beta-hydroxy ester compound. The synthesis method is safe and simple to operate, raw materials are easy to obtain, the price is low, the reaction efficiency is high, and the yield can reach 90% or above and even reach 98%; the method is good in functional group adaptability, wide in substrate adaptability, environmentally friendly, beneficial to industrial production and wide in application in medicine and organic synthesis.

Access to β-Hydroxyl Esters via Copper-Catalyzed Reformatsky Reaction of Ketones and Aldehydes

An efficient and simple Cu-catalyzed Reformatsky reaction of ketones and aldehydes has been accomplished with ethyl iodoacetate. Excellent yields of β-hydroxyl esters were achieved with a range of ketones and aldehydes, which varied from aromatic to aliphatic, unsaturated to saturated ketones and aldehydes. This practical and convenient transformation was conducted with inexpensive, readily available, and commercial starting materials under mild reaction conditions.

One-pot enol silane formation-Mukaiyama aldol reactions: Crossed aldehyde-aldehyde coupling, thioester substrates, and reactions in ester solvents

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) and a trialkylamine base promote both in situ enol silane/silyl ketene acetal formation and Mukaiyama aldol addition reactions between a variety of reaction partners in a single reaction flask. Isolation of the required enol silane or silyl ketene acetal is not necessary. For example, crossed aldol reactions between α-disubstituted aldehydes and non-enolizable aldehydes yield β-hydroxy aldehydes in good yield. In a related reaction, the common laboratory solvent ethyl acetate functions as both an enolate precursor and a green reaction solvent. When thioesters are employed as enolate precursors, high yields for additions to non-enolizable aldehydes are routinely observed.

Bu 4 N + -Controlled Addition and Olefination with Ethyl 2-(Trimethylsilyl)acetate via Silicon Activation

Catalytic Bu 4 NOAc as silicon activator of ethyl 2-(trimethylsilyl)acetate, in THF, was utilized for the synthesis of β-hydroxy esters, whereas employing catalytic Bu 4 NOTMS gave α,β-unsaturated esters. The established reaction conditions were applicable to a diverse range of aromatic, heteroaromatic, aliphatic aldehydes and ketones. Reactions were achieved at room temperature without taking any of the specialized precautions that are in place for other organometallics. A stepwise olefination pathway via silylated β-hydroxy esters with subsequent elimination to form the α,β-unsaturated ester has been demonstrated. The key to selective product formation lies in use of the weaker acetate activator which suppresses subsequent elimination whereas stronger TMSO - activator (and base) facilitates both addition and elimination steps. The use of tetrabutyl ammonium salts for both acetate and trimethylsilyloxide activators provide enhanced silicon activation when compared to their inorganic cation counterparts.

Asymmetric Total Syntheses of the trans -2-Aryl-6-alkyltetrahydropyrans Diospongin B and Parvistones D and e from a Common Precursor

Asymmetric total syntheses of diospongin B and parvistones D and E are reported. Our strategy features a high-yielding three-step reaction sequence: Achmatowicz rearrangement, reductive γ-deoxygenation, and Matsuda-Heck coupling to construct the rare and challenging trans-2-aryl-6-alkyltetrahydropyrans, which serve as common intermediates for the syntheses of diospongin B, and parvistones D and E.

Mechanochemically Initiated Achmatowicz Rearrangement

The Achmatowicz rearrangement converts furfuryl alcohols, obtainable from renewable carbohydrates, into 6-hydroxy-2H-pyrane-3(6H)-ones, which are versatile intermediates for organic synthesis. We describe here the first examples of a solvent-free mechanochemical Achmatowicz rearrangement. Furfuryl alcohols were prepared from furfurals using mechanochemically initiated reductions and Reformatsky reactions. Mechanochemical reaction conditions for the Achmatowicz rearrangement of the obtained furfuryl alcohols were optimized and applied to a series of derivatives, yielding the corresponding rearrangement products in yields of 39 to 95%. GRAPHICAL ABSTRACT.

Processes for the preparation of optically active cyclopentenones and cyclopentenones prepared therefrom

The present invention relates to novel processes for preparing optically active Cyclopentenones of Formula (R)-1, which are useful for the preparation of Prostaglandins and analogs thereof. The invention also relates to novel Cyclopentenones prepared from the processes.