1699-58-7

Usage

Uses

Used in Organic Synthesis:
3,4-bis(benzyloxy)benzyl alcohol is used as a building block for the construction of complex molecular structures in organic synthesis. Its unique chemical reactivity allows for the creation of a wide range of organic compounds.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 3,4-bis(benzyloxy)benzyl alcohol is utilized as a key intermediate in the synthesis of various drugs. Its ability to form carbon-carbon bonds and its potential for functionalization make it a valuable component in the development of new medicinal compounds.
Used in Chemical Reactions:
3,4-bis(benzyloxy)benzyl alcohol is employed as a reagent in chemical reactions, particularly for the formation of carbon-carbon bonds. This contributes to the synthesis of biologically active molecules, which are essential in various chemical and pharmaceutical applications.
Used in Drug Development:
3,4-bis(benzyloxy)benzyl alcohol is used in the development of new drugs due to its diverse chemical properties. Its potential for modification and functionalization allows researchers to explore its use in creating novel therapeutic agents.
Used in Material Science:
In the field of material science, 3,4-bis(benzyloxy)benzyl alcohol has potential applications in the development of new materials. Its unique properties and reactivity can be harnessed to create innovative materials with specific characteristics for various industrial applications.

InChI:InChI=1/C21H20O3/c22-14-19-11-12-20(23-15-17-7-3-1-4-8-17)21(13-19)24-16-18-9-5-2-6-10-18/h1-13,22H,14-16H2

Upstream product

• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 882427-72-7 3,4-(bisbenzyloxy)benzoic acid benzyl ester 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 2150-43-8 3,4-dihydroxybenzoic acid methyl ester 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 54544-05-7 3,4-bis-benzyloxybenzoic acid methyl ester 

Downstream Products

• 150258-69-8 1,2-bis(benzyloxy)-4-(bromomethyl)benzene 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 1129-53-9 3,4-dihydroxyphenylacetamide 
• 1609033-29-5 C₂₅H₂₇NO₂ 
• 78178-56-0 3,4-dibenzyloxy-phenylacetyl chloride 
• 1250409-46-1 1,2-bis(benzyloxy)-5-bromomethyl-4-iodobenzene 

Relevant academic research and scientific papers

Designing new analogs for streamlining the structure of cytotoxic lamellarin natural products

Despite the therapeutic potential of marine-derived lamellarin natural products, their preclinical development has been hampered by their lipophilic nature, causing very poor aqueous solubility. In order to develop more drug-like analogs, their structure was streamlined in this study from both the cytotoxic activity and lipophilicity standpoints. First, a modified total synthetic route was successfully devised to construct a library of 59 systematically designed lamellarin analogs, which were then subjected to cytotoxicity and log P determinations. Along with the 25 first-generation lamellarins previously synthesized in our laboratory, the structure-activity and structure-lipophilicity relationships were extensively evaluated. Our results clearly indicated the additional structural requirements around the lamellarin skeleton which, when combined with those reported previously, can provide invaluable guidance for further modifications to increase the aqueous solubility of these compounds.

Caffeinated compounds and compositions for treatment of amyloid diseases and synucleinopathies

Compounds and their pharmaceutically acceptable salts for treatment of β-amyloid diseases, such as observed in Alzheimer's disease and synucleinopathies, such as Parkinson's disease.

CAFFEINATED COMPOUNDS AND COMPOSITIONS FOR TREATMENT OF AMYLOID DISEASES AND SYNUCLEINOPATHIES

Compounds and their pharmaceutically acceptable salts for treatment of Beta-amyloid diseases, such as observed in Alzheimer's disease and synucleinopathies, such as Parkinson's disease

Synthesis and electrochemical investigation of phthalocyanines with dendritic bulky ethereal substituents

Metal-free and metallophthalocyanines carrying four dendritic 3,4-bis(benzyloxy)benzyloxy groups on the periphery were prepared by cyclotetramerization of a new precursor, namely 4-[3,4-bis(benzyloxy)benzyloxy] phthalonitrile (2) in the presence of the corresponding divalent metal salts (Zn(II), Co(II)). The novel phthalonitrile derivative 2 was synthesized by the reaction of 4-nitrophthalonitrile and 3,4-dibenzyloxybenzyl alcohol (1), which was prepared by the catalytic reduction of 3,4-dibenzyloxybenzaldehyde with NaBH4 in ethanol. The new compounds were characterized by elemental analysis, together with FT-IR, 1H NMR and UV-Vis spectra. The electrochemical and in situ spectroelectrochemical measurements showed that while the cobalt phthalocyanine complex (5) gives both metal-based and ring-based redox processes, the metal-free and zinc phthalocyanine complexes (3 and 4) give only ring-based electron transfer processes. An in situ electrocolorimetric method was applied to investigate the colour of the electrogenerated anionic and cationic forms of the novel phthalocyanine complexes carrying bulky ethereal aryloxy substituents.

NO-CARRIER-ADDED NUCLEOPHILIC [F-18] FLUORINATION OF AROMATIC COMPOUNDS

Phenyliodonium ylide derivatives substituted with electron donating as well as electron withdrawing groups on the aromatic ring are shown for use as precursors in aromatic nucleophilic substitution reactions. The iodonium ylide group is substituted by nucleophiles such as halide ions to provide the corresponding haloaryl derivatives. No- carrier-added [F-18]fluoride ion exclusively substitutes the iodonium ylide moiety in these derivatives and provides high specific activity F- 18 labeled fluoro derivatives. Protected L-dopa-6-iodonium ylide derivative have been synthesized as a precursors for the preparation of no-carrier-added 6-[F- 18]fluoro-L-dopa. The iodonium ylide group in this L-dopa.derivative is nucleophilically substituted by no-carrier-added [F-18]fluoride ion to provide a [F-18]fluoro intermediates which upon acid hydrolysis yielded 6-[F- 18]fluoro-L-dopa.

Synthesis and retrostructural analysis of libraries of AB3 and constitutional isomeric AB2 phenylpropyl ether-based supramolecular dendrimers

We report the synthesis of methyl esters of 3-(4-hydroxyphenyl)propionic, 3-(3,4-dihydroxyphenyl)propionic, 3-(3,5-dihydroxyphenyl)propionic, and 3-(3,4,5-trihydroxyphenyl)propionic acids and their use in a convergent iterative strategy to prepare up to four generations of three libraries, one of 3,4,5- and two of constitutional isomeric 3,4- and 3,5-substituted 3-phenylpropyl dendrons. Each library contains 3-[3,4,5-tris(dodecyl-1-oxy) phenyl]propyl-, 3-[3,4-bis(dodecyl-1-oxy)phenyl]propyl-, 3-{3,4-bis[3-(4- dodecyl-1-oxyphenyl)propyl-1-oxy]phenyl}propyl-, and 3-{3,4,5-tris[3-(4-dodecyl- 1-oxyphenyl)propyl-1-oxy]phenyl}propyl ether first-generation dendrons on their periphery and -CO2CH3, -COOH, and -CH2OH groups at their apex. Regardless of their generation number and their periphery, internal, and apex structures, these dendrons self-assemble into supramolecular dendrimers that self-organize into all periodic and quasi-periodic assemblies encountered previously and in several unencountered with architecturally related benzyl ether-based supramolecular dendrimers. A variety of porous columnar lattices that were previously obtained only from dendritic dipeptides and hollow supramolecular spheres were also discovered from these building blocks. The more flexible and less compact 3-phenylpropyl ether repeat units are stable under acidic conditions, facilitate a simpler synthetic strategy, provide faster dynamics of self-assembly into higher-order supramolecular structures of larger dimensions, exhibit lower transition temperatures than the corresponding benzyl ether homologues, and demonstrate the generality of the self-assembly concept based on amphiphilic dendrons.

Synthesis and antioxidant activity of 4-[2-(3,5-dimethoxyphenyl)ethenyl]-1, 2-benzenediol, a metabolite of Sphaerophysa salsula

4-[2-(3,5-Dimethoxyphenyl)ethenyl]-1,2-benzenediol (7), a stilbene isolated from Sphaerophysa salsula, was synthesized from 3,4-dihydroxybenzaldehyde (1) in five steps in an overall yield of 33%. The spectral data for synthetic 7 are in good agreement with those of the natural product. Hydroxystilbene 7 showed potent antioxidative activity.

New optically active 2H-azirin-3-amines as synthons for enantiomerically pure 2,2-disubstituted glycines: Synthesis of synthons for Tyr(2Me) and Dopa(2Me), and their incorporation into dipeptides

The synthesis of novel unsymmetrically 2,2-disubstituted 2H-azirin-3-amines with chiral auxiliary amino groups is described. Chromatographic separation of the mixture of diastereoisomers yielded (1′R,2S)-2a,b and (1′R.2R)-2a,b (c.f. Scheme 1 and Table 1), which are synthons for (S)- and (R)-2-methyltyrosine and 2-methyl-3′,4′-dihydroxyphenylalanine. Another new synthon 2c, i.e., a synthon for 2-(azidomethyl)alanine, was prepared but could not be separated into its pure diastereoisomers. The reaction of 2 with thiobenzoic acid, benzoic acid, and the amino acid Fmoc-Val-OH yielded the monothiodiamides 11, the diamides 12 (cf. Scheme 3 and Table 3), and the dipeptides 13 (cf. Scheme 4 and Table 4), respectively. From 13, each protecting group was removed selectively under standard conditions (cf. Schemes 5-7 and Tables 5-6). The configuration at C(2) of the amino acid derivatives (1R,1′R)-11a, (1R,1′R)-11b, (1S,1′R)-12b, and (1R,1′R)-12b was determined by X-ray crystallography relative to the known configuration of the chiral auxiliary group.

Design, synthesis and antiproliferative activity of tripentones: A new series of antitubulin agents

Structure-activity relationship studies of a new series of tripentones (thieno[2,3-b]pyrrolizin-8-ones), led us to prepare several derivatives with antiproliferative activities. The most promising 3-(3-hydroxy-4-methoxyphenyl)thieno[2,3-b]pyrrolizin-8-one 20 (leukemia L1210, IC50 = 15 nM) was shown to be a potent inhibitor of tubulin polymerization.