35942-94-0

Usage

Uses

Used in Pharmaceutical Industry:
2-Furanethanol, 5-Methylis used as a synthetic intermediate for the preparation of selective androgen receptor modulators. These modulators exhibit antagonist activity in some types of hormone-dependent tumors, making them a promising option for cancer treatment.
In the synthetic preparation of these compounds, 2-Furanethanol, 5-Methylplays a crucial role in the development of new drugs that can target specific hormone receptors, potentially leading to more effective and targeted cancer therapies.

Upstream product

• 625-86-5 2,5-dimethylfuran 
• 50-00-0 formaldehyd 
• 75-21-8 oxirane 
• 534-22-5 2-methylfuran 
• 53906-90-4 ethyl 2-(5-methylfuran-2-yl)acetate 
• 385440-81-3 2-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-5-methylfuran 
• 1051398-24-3 α-benzyloxy-γ-ketoaldehyde 

Downstream Products

• 120049-55-0 5-Methyl-2-furanethanol 4-methylbenzenesulfonate 
• 406224-43-9 2-Methyl-5-[2-[4-(trifluoromethyl)phenoxy]ethyl]furan 
• 67406-37-5 C₇H₈O₂ 

Relevant academic research and scientific papers

Palladium-Catalyzed Dearomatizing Alkoxydiarylation of Furan Rings by Coupling with Arylboronic Acids: Access to Polysubstituted Oxabicyclic Compounds

We report a protocol for palladium-catalyzed dearomatizing alkoxydiarylation of furan rings via aerobic oxidative coupling between arylboronic acids and 5-aryl-2-hydroxyalkylfurans. This green protocol starting from furan derivatives, which can be sustainably sourced, provides rapid access to polysubstituted 2,3,3a,6a-tetrahydrofuro[3,2-b]furans and hexahydrofuro[3,2-b]furans, oxabicyclic frameworks that are shared by various natural products and synthetic molecules with important biological activities. (Figure presented.).

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.

Singlet oxygen initiated cascade transformation of a simple difuran into the key ABC-ring motif of the pectenotoxins

The key ABC-ring motif of the pectenotoxins has been synthesized, starting from a simple and readily accessible difuran precursor, using a complex singlet oxygen-mediated cascade reaction sequence.

Gold catalysis: benzanellation versus alkylidenecyclopentenone synthesis

A series of different furan-yn-ols were prepared by a three-step sequence. Their reaction with Gagosz's catalyst Ph3PAuNTf2 depends strongly on the substitution pattern of the substrate and the quality of the leaving group. Benzofurans, alkylidenecyclopentenones or Meyer-Schuster type products can be obtained. Improving the leaving group quality leads to the preferred formation of benzofurans.

Diastereoselective, three-component cascade synthesis of tetrahydrofurans and tetrahydropyrans employing the tandem Mukaiyama aldol-lactonization process

(Chemical Equation Presented) A full account of studies leading to the development of a cascade sequence that generates as many as two C-C bonds, one C-O bond, and three new stereocenters providing substituted tetrahydrofurans (THFs) from simple γ-ketoaldehydes and thiopyridyl ketene acetals is described. The process involves a tandem Mukaiyama aldol-lactonization (TMAL) and accumulated evidence suggests the intermediacy of a silylated β-lactone that is intercepted by the pendant ketone. Formation of a cyclic oxocarbenium is followed by reduction with silicon-based nucleophiles leading to a highly diastereoselective synthesis of tetrahydrofurans. This cascade process has now been extended to the synthesis of tetrahydropyrans from simple δ-ketoaldehydes. The stereochemical outcome of the cascade processes described was determined by NOE correlations, coupling constant analysis, and X-ray crystallography of the derived oxygen heterocycles and is in accord with established and recently proposed models for nucleophilic additions to cyclic 5- and 6-membered oxocarbenium ions. The utility of this process was demonstrated by the synthesis of the tetrahydrofuran fragment of colopsinol B.

FUSED HETEROCYCLIC COMPOUNDS USEFUL AS MODULATORS OF NUCLEAR HORMONE RECEPTOR FUNCTION

Disclosed are fused heterocyclic compounds of Formula (I) or pharmaceutically-acceptable salts or stereoisomers thereof. Also disclosed are methods of using such compounds in the treatment of at least one androgen receptor-associated condition, such as, for example, cancer, and pharmaceutical compositions comprising such compounds.

Gold catalysis: Dihydroisobenzofurans and isochromanes by the intramolecular furan/alkyne reaction

A series of furyl alcohols and homofuryl alcohols was synthesized by reduction of furfurals or reaction of furyllithium compounds with epoxides and subsequent propargylation. The gold-catalyzed cycloisomerization of these products furnished dihydroisobenzofurans and isochromanes. Crystal structure analyses proved the sequence of the substituents for both classes of products. Unsaturated dicarbonyl compounds as side-products show the mechanistic relationship to the analogous platinum-catalyzed reactions. Neither ester groups, even on the 4-position of the furan ring, nor aryl bromides hinder the catalysis by gold. In the case of a substrate with an allyl ether in the side chain, a side-product, which provides evidence for a reaction of the alkyne with an inverse regioselectivity, was observed.

METHODS FOR THE SYNTHESIS OF HETEROAROMATIC COMPOUNDS

Methods of making heteroaromatic compounds comprising a 5- membered ring, and dihydro forms thereof, by a metal catalysed 5-endo-cyclisation of alkynes (acetylenes) are disclosed. The methods involve the use of a catalyst comprising a silver salt, more preferably a silver (I) salt, which is employed as a heterogeneous catalyst for the cyclisation reaction. The methods can produce different types of heteroaromatic compounds and are capable of producing highly substituted products, i.e. products in which the 5-membered ring is disubstituted, trisubstituted or, with further simple reactions, tetrasubstituted. The methods described herein generally the advantages that they use conditions and reagents that are benign, cheap and flexible and amenable to scale up, and in which the only by-product is water.

METHOD FOR THE PREPARATION OF FUSED HETEROCYCLIC SUCCINIMIDE COMPOUNDS AND ANALOGS THEREOF

Fused cyclic compounds, methods of using such compounds in the treatment of nuclear hormone receptor-associated conditions such as cancer and immune disorders, and pharmaceutical compositions containing such compounds.

Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function

Fused cyclic compounds, methods of using such compounds in the treatment of nuclear hormone receptor-associated conditions such as cancer and immune disorders, and pharmaceutical compositions containing such compounds.